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Author(s): Lubineau A; Auge J
Title: Water as solvent in organic synthesis
Source: MODERN SOLVENTS IN ORGANIC SYNTHESIS 206: 1-39
Date: 1999
Document Type: Book in series : Review
DOI:
Language: English
Comment:
Address: Univ Paris 11, Lab Chim Organ Multifonct, F-91405 Orsay, France.
Univ Cergy Pontoise, F-95031 Cergy Pontoise, France. Reprint: Lubineau, A, Univ Paris 11, Lab Chim Organ Multifonct, Bat 420, F-91405
Orsay, France. E-mail: lubin@icmo.u-psud.fr
auge@u-cergy.fr Author Keywords:
KeyWords Plus:
Abstract: Organic reactions using water as solvent are reviewed with a focus on pericyclic reactions, carbonyl additions, stoichiometric organometallic reactions, oxidations and reductions which show an unusual outcome in terms of reactivity and selectivity compared with those performed in organic solvent. The advantages of using water as a solvent are discussed and related to the hydrophobic effects and the hydrogen-bonding ability of water with a special emphasis on its very high cohesive energy density which strongly favors organic reactions having a negative activation volume.
Cited References: AKIYAMA T, 1997, TETRAHEDRON LETT, V38, P853 ARAKI S, 1992, B CHEM SOC JPN, V65, P1736 AUGE J, 1994, TETRAHEDRON LETT, V35, P7947 BALLINI R, 1996, TETRAHEDRON LETT, V37, P8027 BALLINI R, 1997, J ORG CHEM, V62, P425 BARBIER P, 1898, CR HEBD ACAD SCI, V128, P110 BELLUCCI C, 1995, TETRAHEDRON LETT, V36, P7289 BENNAIM A, 1965, J PHYS CHEM-US, V69, P3240 BENYEI A, 1990, J MOL CATAL, V58, P151 BERNAL JD, 1964, P ROY SOC LOND A MAT, V280, P299 BIEBER LW, 1998, TETRAHEDRON LETT, V39, P3655 BINDER WH, 1994, TETRAHEDRON, V50, P749 BLAKE JF, 1979, BIOCHEMISTRY-US, V18, P5191 BLAKE JF, 1991, J AM CHEM SOC, V113, P7430 BLAKE JF, 1994, J ORG CHEM, V59, P803 BLOKZIJL W, 1991, J AM CHEM SOC, V113, P4241 BLOKZIJL W, 1992, J AM CHEM SOC, V114, P5440 BLOKZIJL W, 1993, ANGEW CHEM INT EDIT, V32, P1545 BOARETTO A, 1985, J ORGANOMET CHEM, V286, P9 BRANDES E, 1988, J CHEM SOC CHEM COMM, P500 BRANDES E, 1989, J ORG CHEM, V54, P515 BRAUN R, 1986, TETRAHEDRON LETT, V27, P1285 BRESLOW R, 1983, TETRAHEDRON LETT, V24, P1901 BRESLOW R, 1984, TETRAHEDRON LETT, V25, P1239 BRESLOW R, 1988, J AM CHEM SOC, V110, P5613 BRESLOW R, 1991, ACCOUNTS CHEM RES, V24, P159 BRESLOW R, 1994, ACS SYM SER, V568, P291 BRYAN VJ, 1996, TETRAHEDRON LETT, V37, P5341 BRYAN VJ, 1997, TETRAHEDRON LETT, V38, P6493 BUONORA PT, 1995, TETRAHEDRON LETT, V36, P4009 BURLINA F, 1997, BIOORG MED CHEM LETT, V7, P247 CAPPS SM, 1998, TETRAHEDRON LETT, V39, P2853 CARLSON HA, 1996, J AM CHEM SOC, V118, P8475 CATIVIELA C, 1996, CHEM SOC REV, V25, P209 CATIVIELA C, 1997, J CHEM SOC PERK MAR, P653 CHAN TH, 1990, ORGANOMETALLICS, V9, P2649 CHAN TH, 1992, CAN J CHEM, V70, P2726 CHAN TH, 1992, J CHEM SOC CHEM 0515, P747 CHAN TH, 1994, CAN J CHEM, V72, P1181 CHOI SK, 1996, J ORG CHEM, V61, P8739 COATES RM, 1987, J AM CHEM SOC, V109, P1160 COPLEY SD, 1987, J AM CHEM SOC, V109, P5008 CRAMER CJ, 1992, J AM CHEM SOC, V114, P8794 DACK MRJ, 1974, J CHEM EDUC, V51, P231 DACK MRJ, 1975, CHEM SOC REV, V4, P211 DAVIDSON DW, 1973, WATER COMPREHENSIVE, V2, P115 DENMARK SE, 1992, TETRAHEDRON LETT, V33, P7729 DIANA SCH, 1996, SYNLETT MAR, P263 DIEGOCASTRO MJ, 1998, TETRAHEDRON LETT, V39, P2211 DIELS O, 1931, LIEBIGS ANN CHEM, V490, P243 DIGNAM KJ, 1978, J ORG CHEM, V43, P388 DUPUY C, 1991, SYNTHETIC COMMUN, V21, P643 DURANT A, 1995, TETRAHEDRON LETT, V36, P4257 EINHORN C, 1987, J ORGANOMET CHEM, V322, P177 FRANK HS, 1945, J CHEM PHYS, V13, P507 FRANKS F, 1975, WATER COMPREHENSIVE, V4, P1 FRINGUELLI F, 1989, GAZZ CHIM ITAL, V119, P249 FRINGUELLI F, 1989, SYNTHETIC COMMUN, V19, P1939 FRINGUELLI F, 1989, TETRAHEDRON LETT, V30, P1427 FRINGUELLI F, 1992, J ORG CHEM, V57, P1198 FRINGUELLI F, 1994, TETRAHEDRON, V50, P11499 GAJEWSKI JJ, 1997, ACCOUNTS CHEM RES, V30, P219 GANIN E, 1995, SYNTHETIC COMMUN, V25, P3149 GAO J, 1994, J AM CHEM SOC, V116, P1563 GAO JM, 1994, J ORG CHEM, V59, P3714 GAO JM, 1996, J ORG CHEM, V61, P9538 GAO Y, 1987, J AM CHEM SOC, V109, P5765 GARNER PP, 1998, ORGANIC SYNTHESIS WA, PCH1 GORDON DM, 1993, J ORG CHEM, V58, P7937 GRASSERT I, 1993, TETRAHEDRON, V49, P6605 GRAZIANO G, 1996, J AM CHEM SOC, V118, P1831 GRIECO PA, 1983, TETRAHEDRON LETT, V24, P1897 GRIECO PA, 1986, J ORG CHEM, V51, P3553 GRIECO PA, 1987, J ORG CHEM, V52, P1378 GRIECO PA, 1987, J ORG CHEM, V52, P5746 GRIECO PA, 1988, J ORG CHEM, V53, P3658 GRIECO PA, 1989, J ORG CHEM, V54, P5849 GRIECO PA, 1991, ALDRICHIM ACTA, V24, P59 GRIECO PA, 1992, J CHEM SOC CHEM COMM, P368 GROSSELIN JM, 1990, J MOL CATAL, V63, PL25 HABERMAN JX, 1997, TETRAHEDRON LETT, V38, P4735 HANESSIAN S, 1996, TETRAHEDRON LETT, V37, P5273 HANESSIAN S, 1997, SYNLETT APR, P351 HANESSIAN S, 1997, SYNLETT APR, P353 HANNESSIAN S, 1994, SYNLETT, P861 HASEGAWA E, 1993, J ORG CHEM, V58, P5008 HOPFF H, 1942, CHEM ABSTR 1046, V36 HOULLEMARE H, 1997, J CHEM SOC P1, P1629 HUNT I, 1991, J CHEM SOC P2, P1051 ISAAC MB, 1995, TETRAHEDRON LETT, V36, P8957 ISAAC MB, 1997, J ORG CHEM, V62, P5333 ISAACS NS, 1994, J CHEM SOC P2, P495 ISHIHARA K, 1993, SYNLETT AUG, P577 JAYARAMAN M, 1997, TETRAHEDRON LETT, V38, P709 JENNER G, 1996, TETRAHEDRON, V52, P13557 KABALKA GW, 1992, TETRAHEDRON LETT, V33, P865 KAMOCHI Y, 1994, CHEM PHARM BULL, V42, P402 KAMOCHI Y, 1995, CHEM PHARM BULL, V43, P1422 KAUZMANN W, 1987, NATURE, V325, P763 KELLER E, 1996, TETRAHEDRON LETT, V37, P1879 KELLER E, 1997, SYNLETT JUL, P842 KENDE AS, 1994, TETRAHEDRON LETT, V35, P8123 KILLINGER TA, 1977, J ORGANOMET CHEM, V124, P131 KIM E, 1993, J ORG CHEM, V58, P5500 KIRSHENBAUM KS, 1985, J ORG CHEM, V50, P1979 KOBAYASHI S, 1992, TETRAHEDRON LETT, V33, P1625 KOBAYASHI S, 1993, TETRAHEDRON LETT, V34, P3755 KOBAYASHI S, 1997, CHEM LETT, P831 KOBAYASHI S, 1997, CHEM LETT, P959 KOBAYASHI S, 1997, TETRAHEDRON LETT, V38, P4559 KOBAYASHI S, 1998, J CHEM SOC CHEM COMM, P19 KUNTZ EG, 1987, CHEMTECH, V17, P570 KUNZ T, 1989, LIEBIGS ANN CHEM, P891 LABINGER JA, 1990, J AM CHEM SOC, V112, P5628 LARPENT C, 1988, TETRAHEDRON, V44, P6107 LARPENT C, 1990, TETRAHEDRON, V46, P6381 LARPENT C, 1993, TETRAHEDRON LETT, V34, P4331 LARSEN SD, 1985, J AM CHEM SOC, V107, P1768 LARSEN SD, 1986, J AM CHEM SOC, V108, P3512 LAVALLEE JF, 1988, TETRAHEDRON LETT, V29, P6033 LEE JC, 1981, J BIOL CHEM, V256, P718 LI CJ, 1991, ORGANOMETALLICS, V10, P2548 LI CJ, 1991, TETRAHEDRON LETT, V32, P7017 LI CJ, 1996, TETRAHEDRON, V52, P5643 LI CJ, 1997, J ORG CHEM, V62, P8632 LI CJ, 1998, TETRAHEDRON, V54, P2347 LIGHT J, 1990, TETRAHEDRON LETT, V31, P2957 LOH TP, 1996, J CHEM SOC CHEM COMM, P1819 LOH TP, 1996, J CHEM SOC CHEM COMM, P2315 LOH TP, 1996, J CHEM SOC CHEM COMM, V16, P1929 LOH TP, 1997, ANGEW CHEM INT EDIT, V36, P980 LOH TP, 1997, TETRAHEDRON LETT, V38, P865 LOH TP, 1997, TETRAHEDRON LETT, V38, P869 LOH TP, 1998, TETRAHEDRON LETT, V39, P1453 LUBINEAU A, 1986, J ORG CHEM, V51, P2142 LUBINEAU A, 1988, TETRAHEDRON, V44, P6065 LUBINEAU A, 1989, TETRAHEDRON, V45, P6697 LUBINEAU A, 1990, J CHEM SOC P1, P3011 LUBINEAU A, 1991, TETRAHEDRON LETT, V32, P7529 LUBINEAU A, 1992, J CHEM SOC P1, P1631 LUBINEAU A, 1992, TETRAHEDRON LETT, V33, P8073 LUBINEAU A, 1993, TETRAHEDRON, V49, P4639 LUBINEAU A, 1994, NEW J CHEM, V18, P279 LUBINEAU A, 1994, TETRAHEDRON, V50, P10265 LUBINEAU A, 1995, J CARBOHYD CHEM, V14, P1295 LUBINEAU A, 1995, J CHEM SOC P1, P2433 LUBINEAU A, 1997, TETRAHEDRON LETT, V38, P8031 LUCHE JL, 1988, TETRAHEDRON LETT, V29, P5373 MACKEITH RA, 1993, J CHEM SOC P1, P313 MAGNIER E, 1998, TETRAHEDRON LETT, V39, P837 MAITRA U, 1994, TETRAHEDRON LETT, V35, P7861 MASUYAMA Y, 1989, TETRAHEDRON LETT, V30, P3437 MASUYAMA Y, 1991, TETRAHEDRON LETT, V32, P225 MASUYAMA Y, 1996, TETRAHEDRON LETT, V37, P7103 MATSUMOTO K, 1981, ANGEW CHEM INT EDIT, V20, P770 MATTES H, 1985, TETRAHEDRON LETT, V26, P5697 MATUBAYASI N, 1994, J AM CHEM SOC, V116, P1450 MCCAGUE R, 1993, TETRAHEDRON LETT, V34, P3785 MINO T, 1997, J ORG CHEM, V62, P2633 MIYAI T, 1997, SYNLETT JUN, P699 MUKAIYAMA T, 1974, J AM CHEM SOC, V96, P7503 NAGEL U, 1986, CHEM BER, V119, P1731 NAKAGAWA M, 1985, CHEM LETT, P391 NEMETHY G, 1962, J CHEM PHYS, V36, P3401 NOKAMI J, 1983, ORGANOMETALLICS, V2, P191 NOKAMI J, 1984, CHEM LETT, P869 ODA Y, 1992, TETRAHEDRON LETT, V33, P97 OKANO T, 1992, TETRAHEDRON LETT, V33, P5547 OTTO S, 1994, J ORG CHEM, V59, P5372 OTTO S, 1995, TETRAHEDRON LETT, V36, P2645 OTTO S, 1996, J AM CHEM SOC, V118, P7702 OTTO S, 1998, J AM CHEM SOC, V120, P4238 PANDEY PS, 1997, TETRAHEDRON LETT, V38, P7237 PAQUETTE LA, 1996, J AM CHEM SOC, V118, P1931 PAQUETTE LA, 1996, J ORG CHEM, V61, P8799 PAQUETTE LA, 1997, J ORG CHEM, V62, P4293 PAQUETTE LA, 1998, HETEROCYCLES, V47, P107 PARKER DT, 1998, ORGANIC SYNTHESIS WA, PCH2 PETRIER C, 1985, J ORG CHEM, V50, P910 PETRIER C, 1985, TETRAHEDRON LETT, V26, P1449 PETRIER C, 1986, TETRAHEDRON LETT, V27, P3149 PRIVALOV PL, 1989, PURE APPL CHEM, V61, P1097 PROUST SM, 1984, AUST J CHEM, V37, P1677 REED KL, 1989, SYNTHETIC COMMUN, V19, P3579 REICHARDT C, 1988, SOLVENTS SOLVENT EFF REN PD, 1997, SYNTHETIC COMMUN, V27, P2761 RIDEOUT DC, 1980, J AM CHEM SOC, V102, P7816 RUBSAM F, 1997, TETRAHEDRON, V53, P2823 SANGWAN NK, 1989, J CHEM SOC P2, P1223 SCHMID W, 1991, J AM CHEM SOC, V113, P6674 SCHNEIDER HJ, 1986, J CHEM SOC CHEM COMM, P1787 SCHNEIDER HJ, 1987, ANGEW CHEM INT EDIT, V26, P896 SEVERANCE DL, 1992, J AM CHEM SOC, V114, P10966 SHARP KA, 1997, J PHYS CHEM B, V101, P4343 SHIGEMASA Y, 1994, TETRAHEDRON LETT, V35, P1263 SINOU D, 1991, J MOL CATAL, V68, PL9 SISKIN M, 1991, SCIENCE, V254, P231 SJOHOLM R, 1994, J CHEM SOC CHEM COMM, P1217 SMITHRUD DB, 1990, PURE APPL CHEM, V62, P2227 STANLEY HE, 1980, J CHEM PHYS, V73, P3404 TAKAYA H, 1978, J AM CHEM SOC, V100, P1765 TANFORD C, 1979, P NATL ACAD SCI USA, V76, P4175 TOUR JM, 1990, J ORG CHEM, V55, P3452 TOUR JM, 1990, TETRAHEDRON LETT, V31, P4719 TYCHOPOULOS V, 1986, SYNTHETIC COMMUN, V16, P1401 UNEYAMA K, 1986, TETRAHEDRON LETT, V27, P2395 VANDERWEL GK, 1996, J ORG CHEM, V61, P9001 WADA M, 1987, J CHEM SOC CHEM COMM, P708 WADA M, 1997, TETRAHEDRON LETT, V38, P8045 WALDMANN H, 1988, ANGEW CHEM INT EDIT, V27, P274 WALDMANN H, 1990, SYNLETT OCT, P627 WALDMANN H, 1991, LIEBIGS ANN CHEM, P1045 WAN KT, 1993, TETRAHEDRON-ASYMMETR, V4, P2461 WATANABE K, 1985, B CHEM SOC JPN, V58, P1401 WHITE WN, 1970, J ORG CHEM, V35, P2196 WIJNEN JW, 1995, TETRAHEDRON LETT, V36, P5389 WIJNEN JW, 1997, J ORG CHEM, V62, P2039 WU SH, 1990, ACTA CHIM SINICA, V48, P372 WU SH, 1990, SYNTHETIC COMMUN, V20, P1279 YAMAMOTO Y, 1983, J AM CHEM SOC, V105, P6963 YANAGISAWA A, 1993, J AM CHEM SOC, V115, P10356 YANG DTC, 1997, SYNTHETIC COMMUN, V27, P1601 YE DY, 1997, J ORG CHEM, V62, P3748 YI XH, 1997, TETRAHEDRON LETT, V38, P4731 YI XH, 1998, J CHEM SOC CHEM COMM, P449 YU LB, 1996, TETRAHEDRON LETT, V37, P2169 YU LB, 1997, J ORG CHEM, V62, P903 ZHOU JY, 1997, SYNTHETIC COMMUN, V27, P1899 ZHU ZL, 1997, J AM CHEM SOC, V119, P3507 |