JP2010511600A5 - - Google Patents
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- JP2010511600A5 JP2010511600A5 JP2009538795A JP2009538795A JP2010511600A5 JP 2010511600 A5 JP2010511600 A5 JP 2010511600A5 JP 2009538795 A JP2009538795 A JP 2009538795A JP 2009538795 A JP2009538795 A JP 2009538795A JP 2010511600 A5 JP2010511600 A5 JP 2010511600A5
- Authority
- JP
- Japan
- Prior art keywords
- bis
- phosphinomethyl
- butylphosphinomethyl
- decyl
- benzene
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- -1 het Chemical group 0.000 claims description 192
- 125000003118 aryl group Chemical group 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 87
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 claims 46
- 229910052698 phosphorus Inorganic materials 0.000 claims 25
- 239000003446 ligand Substances 0.000 claims 17
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 17
- 125000004429 atom Chemical group 0.000 claims 15
- 125000001424 substituent group Chemical group 0.000 claims 14
- IHOMKOPTBSYOCI-UHFFFAOYSA-N [Fe].c1cccc1.c1ccc(c1)C1=CC=CC=C1 Chemical compound [Fe].c1cccc1.c1ccc(c1)C1=CC=CC=C1 IHOMKOPTBSYOCI-UHFFFAOYSA-N 0.000 claims 12
- 238000000034 method Methods 0.000 claims 12
- DOUYOVFHQKVSSJ-UHFFFAOYSA-N [Fe].c1cccc1.CC(C)(C)c1cccc1 Chemical compound [Fe].c1cccc1.CC(C)(C)c1cccc1 DOUYOVFHQKVSSJ-UHFFFAOYSA-N 0.000 claims 10
- 239000011574 phosphorus Substances 0.000 claims 9
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 7
- 125000005647 linker group Chemical group 0.000 claims 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- 239000003054 catalyst Substances 0.000 claims 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 5
- 150000001875 compounds Chemical class 0.000 claims 4
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 125000004437 phosphorous atom Chemical group 0.000 claims 4
- 125000002947 alkylene group Chemical group 0.000 claims 3
- 229910052787 antimony Inorganic materials 0.000 claims 3
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims 3
- 229910052785 arsenic Inorganic materials 0.000 claims 3
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 claims 3
- 150000001721 carbon Chemical group 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 125000006413 ring segment Chemical group 0.000 claims 3
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 150000001450 anions Chemical class 0.000 claims 2
- 125000000732 arylene group Chemical group 0.000 claims 2
- 229910052751 metal Inorganic materials 0.000 claims 2
- 239000002184 metal Substances 0.000 claims 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 2
- PCHMFMSIIFSBTO-UHFFFAOYSA-N 4-[2,3-ditert-butyl-4-(phosphanylmethyl)phenyl]benzoyl chloride Chemical compound CC(C)(C)C1=C(CP)C=CC(C=2C=CC(=CC=2)C(Cl)=O)=C1C(C)(C)C PCHMFMSIIFSBTO-UHFFFAOYSA-N 0.000 claims 1
- WMKVBJREKBIAID-UHFFFAOYSA-N C(C)(C)(C)C1=C(C(=C(C=C1)CP)C(C)(C)C)C1=C(C(=CC=C1)C(P)(C(C)(C)C)C(C)(C)C)C(P)(C(C)(C)C)C(C)(C)C Chemical compound C(C)(C)(C)C1=C(C(=C(C=C1)CP)C(C)(C)C)C1=C(C(=CC=C1)C(P)(C(C)(C)C)C(C)(C)C)C(P)(C(C)(C)C)C(C)(C)C WMKVBJREKBIAID-UHFFFAOYSA-N 0.000 claims 1
- BPKCUMWXYFFPCK-UHFFFAOYSA-N C(C)(C)(C)C=1C(=C(C=CC1C1=CC(=C(C=C1)C(P)(C(C)(C)C)C(C)(C)C)C(P)(C(C)(C)C)C(C)(C)C)CP)C(C)(C)C Chemical compound C(C)(C)(C)C=1C(=C(C=CC1C1=CC(=C(C=C1)C(P)(C(C)(C)C)C(C)(C)C)C(P)(C(C)(C)C)C(C)(C)C)CP)C(C)(C)C BPKCUMWXYFFPCK-UHFFFAOYSA-N 0.000 claims 1
- PQUURLDEBAJQHI-UHFFFAOYSA-N C(C)(C)(C)C=1C(=C(C=CC1CP)CP)C(C)(C)C Chemical compound C(C)(C)(C)C=1C(=C(C=CC1CP)CP)C(C)(C)C PQUURLDEBAJQHI-UHFFFAOYSA-N 0.000 claims 1
- SYNUGNZEUDMWOZ-UHFFFAOYSA-N C(C)(C)(C)P(C(C)(C)C)C[C-]1C(=CC(=C1C(C)(C)C)C(C)(C)C)CP(C(C)(C)C)C(C)(C)C.[CH-]1C=CC=C1.[Fe+2] Chemical compound C(C)(C)(C)P(C(C)(C)C)C[C-]1C(=CC(=C1C(C)(C)C)C(C)(C)C)CP(C(C)(C)C)C(C)(C)C.[CH-]1C=CC=C1.[Fe+2] SYNUGNZEUDMWOZ-UHFFFAOYSA-N 0.000 claims 1
- FVYXAQRJYVRFPQ-UHFFFAOYSA-N C12(CC3CC(CC(C1)C3)C2)P(C23CC1CC(CC(C2)C1)C3)CC3(C(CC(C(=C3)[Si](C)(C)C)([Si](C)(C)C)C3=CC=CC=C3)(CP(C31CC2CC(CC(C3)C2)C1)C12CC3CC(CC(C1)C3)C2)CP(C23CC1CC(CC(C2)C1)C3)C31CC2CC(CC(C3)C2)C1)CP(C12CC3CC(CC(C1)C3)C2)C23CC1CC(CC(C2)C1)C3 Chemical compound C12(CC3CC(CC(C1)C3)C2)P(C23CC1CC(CC(C2)C1)C3)CC3(C(CC(C(=C3)[Si](C)(C)C)([Si](C)(C)C)C3=CC=CC=C3)(CP(C31CC2CC(CC(C3)C2)C1)C12CC3CC(CC(C1)C3)C2)CP(C23CC1CC(CC(C2)C1)C3)C31CC2CC(CC(C3)C2)C1)CP(C12CC3CC(CC(C1)C3)C2)C23CC1CC(CC(C2)C1)C3 FVYXAQRJYVRFPQ-UHFFFAOYSA-N 0.000 claims 1
- ZIKHDOLERGJDEU-UHFFFAOYSA-N C12(CC3CC(CC(C1)C3)C2)P(C23CC1CC(CC(C2)C1)C3)C[C-]3C(=CC(=C3C3=CC=CC=C3)C3=CC=CC=C3)CP(C31CC2CC(CC(C3)C2)C1)C12CC3CC(CC(C1)C3)C2.[CH-]2C=CC=C2.[Fe+2] Chemical compound C12(CC3CC(CC(C1)C3)C2)P(C23CC1CC(CC(C2)C1)C3)C[C-]3C(=CC(=C3C3=CC=CC=C3)C3=CC=CC=C3)CP(C31CC2CC(CC(C3)C2)C1)C12CC3CC(CC(C1)C3)C2.[CH-]2C=CC=C2.[Fe+2] ZIKHDOLERGJDEU-UHFFFAOYSA-N 0.000 claims 1
- WGPLETPAUNBEAR-UHFFFAOYSA-N CC12CC3OC(C1(CP)C4=C(C=C(C=C4)C(C)(C)C)CP(C56CC7CC(C5)CC(C7)C6)C89CC1CC(C8)CC(C1)C9)(CC(O3)(O2)C)C Chemical compound CC12CC3OC(C1(CP)C4=C(C=C(C=C4)C(C)(C)C)CP(C56CC7CC(C5)CC(C7)C6)C89CC1CC(C8)CC(C1)C9)(CC(O3)(O2)C)C WGPLETPAUNBEAR-UHFFFAOYSA-N 0.000 claims 1
- TZFYBPDAUIGLPQ-UHFFFAOYSA-N CC12CC3OC(C1(CP)C4=C(C=C(C=C4)[Si](C)(C)C)CP(C56CC7CC(C5)CC(C7)C6)C89CC1CC(C8)CC(C1)C9)(CC(O3)(O2)C)C Chemical compound CC12CC3OC(C1(CP)C4=C(C=C(C=C4)[Si](C)(C)C)CP(C56CC7CC(C5)CC(C7)C6)C89CC1CC(C8)CC(C1)C9)(CC(O3)(O2)C)C TZFYBPDAUIGLPQ-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims 1
- NZYVKWHJZSIFDW-UHFFFAOYSA-N PCC1(C2(CC3(OC(CC1(O3)C(F)(F)F)(O2)C(F)(F)F)C(F)(F)F)C(F)(F)F)C2=C(C=C(C(=C2)C2=CC=CC=C2)C2=CC=CC=C2)C2(C3(CC1(OC(CC2(O1)C(F)(F)F)(O3)C(F)(F)F)C(F)(F)F)C(F)(F)F)CP Chemical compound PCC1(C2(CC3(OC(CC1(O3)C(F)(F)F)(O2)C(F)(F)F)C(F)(F)F)C(F)(F)F)C2=C(C=C(C(=C2)C2=CC=CC=C2)C2=CC=CC=C2)C2(C3(CC1(OC(CC2(O1)C(F)(F)F)(O3)C(F)(F)F)C(F)(F)F)C(F)(F)F)CP NZYVKWHJZSIFDW-UHFFFAOYSA-N 0.000 claims 1
- RCRMKTGLHVLPDR-UHFFFAOYSA-N PCC1(C2(CC3(OC(CC1(O3)C(F)(F)F)(O2)C(F)(F)F)C(F)(F)F)C(F)(F)F)C2=C(C=C(C(=C2)[Si](C)(C)C)[Si](C)(C)C)C2(C3(CC1(OC(CC2(O1)C(F)(F)F)(O3)C(F)(F)F)C(F)(F)F)C(F)(F)F)CP Chemical compound PCC1(C2(CC3(OC(CC1(O3)C(F)(F)F)(O2)C(F)(F)F)C(F)(F)F)C(F)(F)F)C2=C(C=C(C(=C2)[Si](C)(C)C)[Si](C)(C)C)C2(C3(CC1(OC(CC2(O1)C(F)(F)F)(O3)C(F)(F)F)C(F)(F)F)C(F)(F)F)CP RCRMKTGLHVLPDR-UHFFFAOYSA-N 0.000 claims 1
- HXPIDDUXKSTDHD-UHFFFAOYSA-N PCC1(C2(CC3(OC(CC1(O3)C(F)(F)F)(O2)C(F)(F)F)C(F)(F)F)C(F)(F)F)C2=C(C=C(C=C2)C(C)(C)C)C2(C3(CC1(OC(CC2(O1)C(F)(F)F)(O3)C(F)(F)F)C(F)(F)F)C(F)(F)F)CP Chemical compound PCC1(C2(CC3(OC(CC1(O3)C(F)(F)F)(O2)C(F)(F)F)C(F)(F)F)C(F)(F)F)C2=C(C=C(C=C2)C(C)(C)C)C2(C3(CC1(OC(CC2(O1)C(F)(F)F)(O3)C(F)(F)F)C(F)(F)F)C(F)(F)F)CP HXPIDDUXKSTDHD-UHFFFAOYSA-N 0.000 claims 1
- VZOAJOYLYZHPTF-UHFFFAOYSA-N PCC1(C2(CC3(OC(CC1(O3)C(F)(F)F)(O2)C(F)(F)F)C(F)(F)F)C(F)(F)F)C2=C(C=C(C=C2)C2=CC=CC=C2)C2(C3(CC1(OC(CC2(O1)C(F)(F)F)(O3)C(F)(F)F)C(F)(F)F)C(F)(F)F)CP Chemical compound PCC1(C2(CC3(OC(CC1(O3)C(F)(F)F)(O2)C(F)(F)F)C(F)(F)F)C(F)(F)F)C2=C(C=C(C=C2)C2=CC=CC=C2)C2(C3(CC1(OC(CC2(O1)C(F)(F)F)(O3)C(F)(F)F)C(F)(F)F)C(F)(F)F)CP VZOAJOYLYZHPTF-UHFFFAOYSA-N 0.000 claims 1
- GMBMVDAIJGKWEY-UHFFFAOYSA-N PCC1(C2(CC3(OC(CC1(O3)C)(O2)C)C)C)[C-]2C(=CC(=C2C2=CC=CC=C2)C2=CC=CC=C2)C2(C3(CC1(OC(CC2(O1)C)(O3)C)C)C)CP.[CH-]3C=CC=C3.[Fe+2] Chemical compound PCC1(C2(CC3(OC(CC1(O3)C)(O2)C)C)C)[C-]2C(=CC(=C2C2=CC=CC=C2)C2=CC=CC=C2)C2(C3(CC1(OC(CC2(O1)C)(O3)C)C)C)CP.[CH-]3C=CC=C3.[Fe+2] GMBMVDAIJGKWEY-UHFFFAOYSA-N 0.000 claims 1
- IYLXXNMTVQJTAO-UHFFFAOYSA-N PCC1(C2(CC3(OC(CC1(O3)C)(O2)C)C)C)[C-]2C(=CC(=C2C2=CC=CC=C2)C2=CC=CC=C2)CP(C(C)(C)C)C(C)(C)C.[CH-]2C=CC=C2.[Fe+2] Chemical compound PCC1(C2(CC3(OC(CC1(O3)C)(O2)C)C)C)[C-]2C(=CC(=C2C2=CC=CC=C2)C2=CC=CC=C2)CP(C(C)(C)C)C(C)(C)C.[CH-]2C=CC=C2.[Fe+2] IYLXXNMTVQJTAO-UHFFFAOYSA-N 0.000 claims 1
- NPHBDKQSRNBIAS-UHFFFAOYSA-N PCC1(C2(CC3OC(CC1(O3)C)(O2)C)C)C2=C(C=C(C(=C2)C2=CC=CC=C2)C2=CC=CC=C2)CP(C(C)(C)C)C(C)(C)C Chemical compound PCC1(C2(CC3OC(CC1(O3)C)(O2)C)C)C2=C(C=C(C(=C2)C2=CC=CC=C2)C2=CC=CC=C2)CP(C(C)(C)C)C(C)(C)C NPHBDKQSRNBIAS-UHFFFAOYSA-N 0.000 claims 1
- GYIWLSMPALCVHA-UHFFFAOYSA-N PCC1(C2(CC3OC(CC1(O3)C)(O2)C)C)C2=C(C=C(C(=C2)[Si](C)(C)C)[Si](C)(C)C)C2(C3(CC1OC(CC2(O1)C)(O3)C)C)CP Chemical compound PCC1(C2(CC3OC(CC1(O3)C)(O2)C)C)C2=C(C=C(C(=C2)[Si](C)(C)C)[Si](C)(C)C)C2(C3(CC1OC(CC2(O1)C)(O3)C)C)CP GYIWLSMPALCVHA-UHFFFAOYSA-N 0.000 claims 1
- RXDJXUGTZPXYGH-UHFFFAOYSA-N PCC1(C2(CC3OC(CC1(O3)C)(O2)C)C)C2=C(C=C(C=C2)C(C)(C)C)CP(C(C)(C)C)C(C)(C)C Chemical compound PCC1(C2(CC3OC(CC1(O3)C)(O2)C)C)C2=C(C=C(C=C2)C(C)(C)C)CP(C(C)(C)C)C(C)(C)C RXDJXUGTZPXYGH-UHFFFAOYSA-N 0.000 claims 1
- JUKIFWJJWCHQOZ-UHFFFAOYSA-N PCC1(C2(CC3OC(CC1(O3)C)(O2)C)C)C2=C(C=C(C=C2)C2=CC=CC=C2)CP(C23CC1CC(CC(C2)C1)C3)C31CC2CC(CC(C3)C2)C1 Chemical compound PCC1(C2(CC3OC(CC1(O3)C)(O2)C)C)C2=C(C=C(C=C2)C2=CC=CC=C2)CP(C23CC1CC(CC(C2)C1)C3)C31CC2CC(CC(C3)C2)C1 JUKIFWJJWCHQOZ-UHFFFAOYSA-N 0.000 claims 1
- KITZKOHPUHSOEI-UHFFFAOYSA-N PCC1(C2(CC3OC(CC1(O3)C)(O2)C)C)C2=C(C=C(C=C2)[Si](C)(C)C)C2(C3(CC1OC(CC2(O1)C)(O3)C)C)CP Chemical compound PCC1(C2(CC3OC(CC1(O3)C)(O2)C)C)C2=C(C=C(C=C2)[Si](C)(C)C)C2(C3(CC1OC(CC2(O1)C)(O3)C)C)CP KITZKOHPUHSOEI-UHFFFAOYSA-N 0.000 claims 1
- FTQYVJBNBRLFLY-UHFFFAOYSA-N PCC1(C2(CC3OC(CC1(O3)C)(O2)C)C)[C-]2C(=CC(=C2C2=CC=CC=C2)C2=CC=CC=C2)C2(C3(CC1OC(CC2(O1)C)(O3)C)C)CP.[CH-]3C=CC=C3.[Fe+2] Chemical compound PCC1(C2(CC3OC(CC1(O3)C)(O2)C)C)[C-]2C(=CC(=C2C2=CC=CC=C2)C2=CC=CC=C2)C2(C3(CC1OC(CC2(O1)C)(O3)C)C)CP.[CH-]3C=CC=C3.[Fe+2] FTQYVJBNBRLFLY-UHFFFAOYSA-N 0.000 claims 1
- SMKMHULWMFELQG-UHFFFAOYSA-N PCC1(C2(CC3OC(CC1(O3)C)(O2)C)C)[C-]2C(=CC(=C2C2=CC=CC=C2)C2=CC=CC=C2)CP(C(C)(C)C)C(C)(C)C.[CH-]2C=CC=C2.[Fe+2] Chemical compound PCC1(C2(CC3OC(CC1(O3)C)(O2)C)C)[C-]2C(=CC(=C2C2=CC=CC=C2)C2=CC=CC=C2)CP(C(C)(C)C)C(C)(C)C.[CH-]2C=CC=C2.[Fe+2] SMKMHULWMFELQG-UHFFFAOYSA-N 0.000 claims 1
- YLGURJYLNZINMJ-UHFFFAOYSA-N [1,3,5,7-tetramethyl-8-[2-[1,3,5,7-tetramethyl-8-(phosphanylmethyl)-2,4,6-trioxatricyclo[3.3.1.13,7]decan-8-yl]-4-trimethylsilylphenyl]-2,4,6-trioxatricyclo[3.3.1.13,7]decan-8-yl]methylphosphane Chemical compound O1C2(C)CC(O3)(C)OC1(C)CC3(C)C2(CP)C1=CC([Si](C)(C)C)=CC=C1C1(CP)C2(C)CC(C)(O3)OC1(C)CC3(C)O2 YLGURJYLNZINMJ-UHFFFAOYSA-N 0.000 claims 1
- SZBXVUKSDKXGMQ-UHFFFAOYSA-N [1,3,5,7-tetramethyl-8-[4-phenyl-2-[1,3,5,7-tetramethyl-8-(phosphanylmethyl)-2,4,6-trioxatricyclo[3.3.1.13,7]decan-8-yl]phenyl]-2,4,6-trioxatricyclo[3.3.1.13,7]decan-8-yl]methylphosphane Chemical compound O1C(C)(O2)CC3(C)OC2(C)CC1(C)C3(CP)C(C(=C1)C2(CP)C3(C)CC4(OC(O3)(C)CC2(C)O4)C)=CC=C1C1=CC=CC=C1 SZBXVUKSDKXGMQ-UHFFFAOYSA-N 0.000 claims 1
- XPLBBAQFWIYEOY-UHFFFAOYSA-N [2,2,4,4-tetramethyl-3-[2-(2,2,4,4-tetramethyl-3-phosphanylpentan-3-yl)-4-tritert-butylsilylphenyl]pentan-3-yl]phosphane Chemical compound CC(C)(C)C(P)(C(C)(C)C)C1=CC=C([Si](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C=C1C(P)(C(C)(C)C)C(C)(C)C XPLBBAQFWIYEOY-UHFFFAOYSA-N 0.000 claims 1
- ZOYPIDOTHFUPMW-UHFFFAOYSA-N [3,4-bis(trimethylsilyl)phenyl]methyl-ditert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)CC1=CC=C([Si](C)(C)C)C([Si](C)(C)C)=C1 ZOYPIDOTHFUPMW-UHFFFAOYSA-N 0.000 claims 1
- GKYVRIAJZUEXJR-UHFFFAOYSA-N [8-(3,4-diphenylphenyl)-1,3,5,7-tetramethyl-2,4,6-trioxatricyclo[3.3.1.13,7]decan-8-yl]methylphosphane Chemical compound O1C(C)(O2)CC3(C)OC2(C)CC1(C)C3(CP)C(C=C1C=2C=CC=CC=2)=CC=C1C1=CC=CC=C1 GKYVRIAJZUEXJR-UHFFFAOYSA-N 0.000 claims 1
- FKUMADLCVKODJS-UHFFFAOYSA-N [8-[4-tert-butyl-2-[1,3,5,7-tetramethyl-8-(phosphanylmethyl)-2,4,6-trioxatricyclo[3.3.1.13,7]decan-8-yl]phenyl]-1,3,5,7-tetramethyl-2,4,6-trioxatricyclo[3.3.1.13,7]decan-8-yl]methylphosphane Chemical compound O1C2(C)CC(O3)(C)OC1(C)CC3(C)C2(CP)C1=CC=C(C(C)(C)C)C=C1C1(CP)C(O2)(C)CC3(C)OC2(C)CC1(C)O3 FKUMADLCVKODJS-UHFFFAOYSA-N 0.000 claims 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- RHKRUKUHXVBJJD-UHFFFAOYSA-N bis(1-adamantyl)-[[2-(ditert-butylphosphanylmethyl)-4,5-bis(trimethylsilyl)phenyl]methyl]phosphane Chemical compound CC(C)(C)P(C(C)(C)C)CC1=CC([Si](C)(C)C)=C([Si](C)(C)C)C=C1CP(C12CC3CC(CC(C3)C1)C2)C1(C2)CC(C3)CC2CC3C1 RHKRUKUHXVBJJD-UHFFFAOYSA-N 0.000 claims 1
- VTVFXNKSLYYIIG-UHFFFAOYSA-N bis(1-adamantyl)-[[2-(ditert-butylphosphanylmethyl)-4,5-diphenylphenyl]methyl]phosphane Chemical compound C=1C=CC=CC=1C=1C=C(CP(C23CC4CC(CC(C4)C2)C3)C23CC4CC(CC(C4)C2)C3)C(CP(C(C)(C)C)C(C)(C)C)=CC=1C1=CC=CC=C1 VTVFXNKSLYYIIG-UHFFFAOYSA-N 0.000 claims 1
- MNPOPASJOFYBMI-UHFFFAOYSA-N bis(1-adamantyl)-[[2-(ditert-butylphosphanylmethyl)-5-phenylphenyl]methyl]phosphane Chemical compound C1=C(CP(C23CC4CC(CC(C4)C2)C3)C23CC4CC(CC(C4)C2)C3)C(CP(C(C)(C)C)C(C)(C)C)=CC=C1C1=CC=CC=C1 MNPOPASJOFYBMI-UHFFFAOYSA-N 0.000 claims 1
- OESSXRJOTGVSMA-UHFFFAOYSA-N bis(1-adamantyl)-[[2-(ditert-butylphosphanylmethyl)-5-trimethylsilylphenyl]methyl]phosphane Chemical compound CC(C)(C)P(C(C)(C)C)CC1=CC=C([Si](C)(C)C)C=C1CP(C12CC3CC(CC(C3)C1)C2)C1(C2)CC(C3)CC2CC3C1 OESSXRJOTGVSMA-UHFFFAOYSA-N 0.000 claims 1
- MXPSHWBHUIQVPY-UHFFFAOYSA-N bis(1-adamantyl)-[[2-[1,3,5,7-tetramethyl-8-(phosphanylmethyl)-2,4,6-trioxatricyclo[3.3.1.13,7]decan-8-yl]-4,5-bis(trimethylsilyl)phenyl]methyl]phosphane Chemical compound C1C(C2)CC(C3)CC2CC13P(C12CC3CC(CC(C3)C1)C2)CC1=CC([Si](C)(C)C)=C([Si](C)(C)C)C=C1C1(CP)C2(C)CC(C)(O3)OC1(C)CC3(C)O2 MXPSHWBHUIQVPY-UHFFFAOYSA-N 0.000 claims 1
- IYJFKBUCDIHNLX-UHFFFAOYSA-N bis(1-adamantyl)-[[2-[bis(1-adamantyl)phosphanylmethyl]-4,5-diphenylphenyl]methyl]phosphane Chemical compound C1C(C2)CC(C3)CC2CC13P(C12CC3CC(CC(C3)C1)C2)CC(C(=CC=1C=2C=CC=CC=2)CP(C23CC4CC(CC(C4)C2)C3)C23CC4CC(CC(C4)C2)C3)=CC=1C1=CC=CC=C1 IYJFKBUCDIHNLX-UHFFFAOYSA-N 0.000 claims 1
- OXOFOTRVVAMBDF-UHFFFAOYSA-N bis(1-adamantyl)-[[2-[bis(1-adamantyl)phosphanylmethyl]-4-trimethylsilylphenyl]methyl]phosphane Chemical compound C1C(C2)CC(C3)CC2CC13P(C12CC3CC(CC(C3)C1)C2)CC1=CC([Si](C)(C)C)=CC=C1CP(C12CC3CC(CC(C3)C1)C2)C1(C2)CC(C3)CC2CC3C1 OXOFOTRVVAMBDF-UHFFFAOYSA-N 0.000 claims 1
- BWSNJKVSHLWCQO-UHFFFAOYSA-N bis(1-adamantyl)-[[5-tert-butyl-2-[1,3,5,7-tetramethyl-8-(phosphanylmethyl)-2,4,6-trioxatricyclo[3.3.1.13,7]decan-8-yl]phenyl]methyl]phosphane Chemical compound O1C2(C)CC(O3)(C)OC1(C)CC3(C)C2(CP)C1=CC=C(C(C)(C)C)C=C1CP(C12CC3CC(CC(C3)C1)C2)C1(C2)CC(C3)CC2CC3C1 BWSNJKVSHLWCQO-UHFFFAOYSA-N 0.000 claims 1
- 229910002091 carbon monoxide Inorganic materials 0.000 claims 1
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- 238000005810 carbonylation reaction Methods 0.000 claims 1
- 239000002131 composite material Substances 0.000 claims 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- GASSJTLSIVRDDT-UHFFFAOYSA-N ditert-butyl-[[2-(ditert-butylphosphanylmethyl)-4,5-dimethyl-3,6-diphenylphenyl]methyl]phosphane Chemical compound CC(C)(C)P(C(C)(C)C)CC=1C(CP(C(C)(C)C)C(C)(C)C)=C(C=2C=CC=CC=2)C(C)=C(C)C=1C1=CC=CC=C1 GASSJTLSIVRDDT-UHFFFAOYSA-N 0.000 claims 1
- XGTLLXBATZZBDJ-UHFFFAOYSA-N ditert-butyl-[[2-(ditert-butylphosphanylmethyl)-4,5-diphenylphenyl]methyl]phosphane Chemical compound C=1C=CC=CC=1C=1C=C(CP(C(C)(C)C)C(C)(C)C)C(CP(C(C)(C)C)C(C)(C)C)=CC=1C1=CC=CC=C1 XGTLLXBATZZBDJ-UHFFFAOYSA-N 0.000 claims 1
- FNVYFXOMLKSSFK-UHFFFAOYSA-N ditert-butyl-[[4,5-diphenyl-2-[1,3,5,7-tetramethyl-8-(phosphanylmethyl)-2,4,6-trioxatricyclo[3.3.1.13,7]decan-8-yl]phenyl]methyl]phosphane Chemical compound C=1C=CC=CC=1C=1C=C(C2(CP)C3(C)CC4(OC(O3)(C)CC2(C)O4)C)C(CP(C(C)(C)C)C(C)(C)C)=CC=1C1=CC=CC=C1 FNVYFXOMLKSSFK-UHFFFAOYSA-N 0.000 claims 1
- MWGNUOVYRKMMRJ-UHFFFAOYSA-N ditert-butyl-[[4,5-ditert-butyl-2-(ditert-butylphosphanylmethyl)phenyl]methyl]phosphane Chemical compound CC(C)(C)P(C(C)(C)C)CC1=CC(C(C)(C)C)=C(C(C)(C)C)C=C1CP(C(C)(C)C)C(C)(C)C MWGNUOVYRKMMRJ-UHFFFAOYSA-N 0.000 claims 1
- CJRKTQKOGOVYTO-UHFFFAOYSA-N ditert-butyl-[[4-tert-butyl-2-(ditert-butylphosphanylmethyl)phenyl]methyl]phosphane Chemical compound CC(C)(C)P(C(C)(C)C)CC1=CC=C(C(C)(C)C)C=C1CP(C(C)(C)C)C(C)(C)C CJRKTQKOGOVYTO-UHFFFAOYSA-N 0.000 claims 1
- HBFGAXXFXLINQU-UHFFFAOYSA-N ditert-butyl-[[5-phenyl-2-[1,3,5,7-tetramethyl-8-(phosphanylmethyl)-2,4,6-trioxatricyclo[3.3.1.13,7]decan-8-yl]phenyl]methyl]phosphane Chemical compound C=1C=C(C2(CP)C3(C)CC4(OC(O3)(C)CC2(C)O4)C)C(CP(C(C)(C)C)C(C)(C)C)=CC=1C1=CC=CC=C1 HBFGAXXFXLINQU-UHFFFAOYSA-N 0.000 claims 1
- YKLBAUXVBKHXAY-UHFFFAOYSA-N ditert-butyl-[[5-tert-butyl-2-[1,3,5,7-tetramethyl-8-(phosphanylmethyl)-2,4,6-trioxatricyclo[3.3.1.13,7]decan-8-yl]phenyl]methyl]phosphane Chemical compound CC(C)(C)P(C(C)(C)C)CC1=CC(C(C)(C)C)=CC=C1C1(CP)C(O2)(C)CC3(C)OC2(C)CC1(C)O3 YKLBAUXVBKHXAY-UHFFFAOYSA-N 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
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- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 claims 1
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- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 claims 1
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- KXFSUVJPEQYUGN-UHFFFAOYSA-N trimethyl(phenyl)silane Chemical compound C[Si](C)(C)C1=CC=CC=C1 KXFSUVJPEQYUGN-UHFFFAOYSA-N 0.000 claims 1
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| GB0716530A GB0716530D0 (en) | 2007-08-24 | 2007-08-24 | Novel carbonylation ligands and their use in the carbonylation of ethylenically unsaturated compounds |
| PCT/GB2007/050717 WO2008065448A1 (en) | 2006-12-02 | 2007-11-27 | Novel carbonylation ligands and their use in the carbonylation of ethylenically unsaturated compounds |
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| EP1957198B1 (en) | 2005-11-17 | 2018-08-22 | Lucite International UK Limited | Carbonylation of ethylenically unsaturated compounds |
| JP2010511600A (ja) | 2006-12-02 | 2010-04-15 | ルーサイト インターナショナル ユーケー リミテッド | 新規のカルボニル化配位子及びエチレン性不飽和化合物のカルボニル化におけるその使用 |
| FR2950349B1 (fr) * | 2009-09-18 | 2011-08-26 | Rhodia Operations | Composes organophosphores, systemes catalytiques comprenant ces composes et procede d'hydrocyanation utilisant ces systemes catalytiques |
| GB0921876D0 (en) * | 2009-12-15 | 2010-01-27 | Lucite Int Uk Ltd | Improved carbonylation process |
| GB201000078D0 (en) * | 2010-01-05 | 2010-02-17 | Lucite Int Uk Ltd | Process for the carbonylation of ethylenically unsaturated compounds, novel carbonylation ligands and catalyst systems incorporatng such ligands |
| EP3441384B1 (de) * | 2017-08-08 | 2019-12-25 | Evonik Operations GmbH | Methoxycarbonylierung mit ameisensäure und methanol |
| EP3441383B1 (de) * | 2017-08-08 | 2019-12-25 | Evonik Operations GmbH | Methoxycarbonylierung mit ameisensäure als co-quelle |
| CN115873221B (zh) * | 2021-12-17 | 2024-06-04 | 浙江新和成股份有限公司 | 一种含磷聚合物及其制备方法和应用 |
| CN116082157B (zh) * | 2023-01-18 | 2025-09-16 | 上海梓龄化工技术有限公司 | 一种烯属不饱和化合物烷氧羰基化反应制备有机羧酸酯的方法 |
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-
2007
- 2007-11-27 JP JP2009538795A patent/JP2010511600A/ja active Pending
- 2007-11-27 WO PCT/GB2007/050717 patent/WO2008065448A1/en not_active Ceased
- 2007-11-27 US US12/517,215 patent/US9809611B2/en not_active Expired - Fee Related
- 2007-11-27 MX MX2009005568A patent/MX2009005568A/es active IP Right Grant
- 2007-11-27 CA CA2671409A patent/CA2671409C/en not_active Expired - Fee Related
- 2007-11-27 ES ES07824927T patent/ES2729615T3/es active Active
- 2007-11-27 EA EA200970528A patent/EA032533B1/ru not_active IP Right Cessation
- 2007-11-27 KR KR1020097012397A patent/KR101464702B1/ko not_active Expired - Fee Related
- 2007-11-27 EP EP07824927.3A patent/EP2097429B1/en not_active Not-in-force
- 2007-11-27 BR BRPI0719344A patent/BRPI0719344B1/pt not_active IP Right Cessation
- 2007-11-27 CN CN201510500201.2A patent/CN105153241B/zh not_active Expired - Fee Related
- 2007-11-27 AU AU2007327051A patent/AU2007327051B2/en not_active Ceased
- 2007-11-29 TW TW096145458A patent/TWI545128B/zh not_active IP Right Cessation
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- 2009-07-01 NO NO20092480A patent/NO20092480L/no not_active Application Discontinuation
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