Total stereochemical control in the addition of thiols to p-toluenesulfonylacetylene. Synthesis of Z-and E-2-sulfanylvinylsulfonyl derivatives

Journal of Organic Chemistry

Volumn 70, Issue 2, 2005, Pages 735-738

  Medel, Rocío ^a   Monterde, María I ^a   Plumet, Joaquín ^a   Rojas, Jenny K ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; MOLECULAR DYNAMICS; REACTION KINETICS; SODIUM COMPOUNDS;

ARYL SULFIDES; CATALYTIC REAGENTS; STEREOCHEMICAL CONTROL;

STEREOCHEMISTRY;

1 [[2 (BENZYLSULFANYL)VINYL]SULFONYL] 4 METHYLBENZENE; 1 [[2 (BENZYLSULFANYL)VINYL]SULFONYL]4 METHYLBENZENE; 1 CHLORO 4 [[[2 (4 METHYLPHENYL)SULFONYL]VINYL]SULFANYL]METHYL]BENZENE; 1 CHLORO 4 [[[2 [(4 METHYLPHENYL)SULFONYL]VINYL]SULFANYL]METHYL]BENZENE; 1 METHOXY 4 [[2 [(4 METHYLPHENYL)SULFONYL]VINYL]SULFANYL]BENZENE; 1 METHOXY 4 [[[2 (4 METHYLPHENYL)SULFONYL]VINYL]SULFANYL]METHYL]BENZENE; 1 METHYL 4 [[2 (OCTYLSULFANYL)]VINYL]SULFONYL]BENZENE; 1 METHYL 4 [[2 (PHENYLSULFANYL)]VINYL]SULFONYL]BENZENE; 1 METHYL 4 [[2 [(4 NITROPHENYL)SULFANYL]VINYL]SULFONYL]BENZENE; ACETYLENE DERIVATIVE; BENZENE DERIVATIVE; SULFONE DERIVATIVE; TOLUENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL REACTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 12344300150     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0402576     Document Type: Article

References (13)

1. See, for instance: (a) Stirling, C. J. M. J. Chem. Soc. 1964, 5856-5862. (b) Truce, W. E.; Tichenor, G. J. W. J. Org. Chem. 1972, 37, 2391-2394. (c) Selling, H. A. Tetrahedron 1975, 31, 2387-2390.
2. See, for instance: (a) Stirling, C. J. M. J. Chem. Soc. 1964, 5856-5862. (b) Truce, W. E.; Tichenor, G. J. W. J. Org. Chem. 1972, 37, 2391-2394. (c) Selling, H. A. Tetrahedron 1975, 31, 2387-2390.
3. See, for instance: (a) Stirling, C. J. M. J. Chem. Soc. 1964, 5856-5862. (b) Truce, W. E.; Tichenor, G. J. W. J. Org. Chem. 1972, 37, 2391-2394. (c) Selling, H. A. Tetrahedron 1975, 31, 2387-2390.
4. Arjona, O.; Medel, R.; Rojas, J. K.; Costa, A. M.; Vilarrasa, J. Tetrahedron Lett. 2003, 44, 6369-6373.
5. Arjona, O.; Iradier, F.; Medel, R.; Plumet, J. J. Org. Chem. 1999, 64, 6090-6093.
6. The UV-irradiation-induced addition of thiols to monosubstituted propargilyc alcohols has been also reported. See: (a) Mantione, R.; Normant, H. Bull. Soc. Chem. Fr. 1973, 2261-2265. For other additions of thiols to alkynes under radical conditions, usually giving stereoisomeric mixtures, see: (b) Kuniyasu, H.; Ogawa, A.; Sato, K.; Ryu, I.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc. 1992, 114, 5902-5903. (c) Kuniyasu, H.; Ogawa, A.; Sato, K.; Ryu, I.; Sonoda, N. Tetrahedron Lett. 1992, 33, 5525-5528. (d) Ogawa, A.; Kudo, A.; Hirao, T. Tetrahedron Lett. 1998, 3, 5213-5216 and references therein. For the uncatalyzed addition to methylpropiolate, see: (e) Kodomari, M.; Saitoh, G.; Yoshitomi, S. Bull. Soc. Chem. Jpn. 1991, 64, 3485-3487.
7. The UV-irradiation-induced addition of thiols to monosubstituted propargilyc alcohols has been also reported. See: (a) Mantione, R.; Normant, H. Bull. Soc. Chem. Fr. 1973, 2261-2265. For other additions of thiols to alkynes under radical conditions, usually giving stereoisomeric mixtures, see: (b) Kuniyasu, H.; Ogawa, A.; Sato, K.; Ryu, I.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc. 1992, 114, 5902-5903. (c) Kuniyasu, H.; Ogawa, A.; Sato, K.; Ryu, I.; Sonoda, N. Tetrahedron Lett. 1992, 33, 5525-5528. (d) Ogawa, A.; Kudo, A.; Hirao, T. Tetrahedron Lett. 1998, 3, 5213-5216 and references therein. For the uncatalyzed addition to methylpropiolate, see: (e) Kodomari, M.; Saitoh, G.; Yoshitomi, S. Bull. Soc. Chem. Jpn. 1991, 64, 3485-3487.
8. The UV-irradiation-induced addition of thiols to monosubstituted propargilyc alcohols has been also reported. See: (a) Mantione, R.; Normant, H. Bull. Soc. Chem. Fr. 1973, 2261-2265. For other additions of thiols to alkynes under radical conditions, usually giving stereoisomeric mixtures, see: (b) Kuniyasu, H.; Ogawa, A.; Sato, K.; Ryu, I.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc. 1992, 114, 5902-5903. (c) Kuniyasu, H.; Ogawa, A.; Sato, K.; Ryu, I.; Sonoda, N. Tetrahedron Lett. 1992, 33, 5525-5528. (d) Ogawa, A.; Kudo, A.; Hirao, T. Tetrahedron Lett. 1998, 3, 5213-5216 and references therein. For the uncatalyzed addition to methylpropiolate, see: (e) Kodomari, M.; Saitoh, G.; Yoshitomi, S. Bull. Soc. Chem. Jpn. 1991, 64, 3485-3487.
9. The UV-irradiation-induced addition of thiols to monosubstituted propargilyc alcohols has been also reported. See: (a) Mantione, R.; Normant, H. Bull. Soc. Chem. Fr. 1973, 2261-2265. For other additions of thiols to alkynes under radical conditions, usually giving stereoisomeric mixtures, see: (b) Kuniyasu, H.; Ogawa, A.; Sato, K.; Ryu, I.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc. 1992, 114, 5902-5903. (c) Kuniyasu, H.; Ogawa, A.; Sato, K.; Ryu, I.; Sonoda, N. Tetrahedron Lett. 1992, 33, 5525-5528. (d) Ogawa, A.; Kudo, A.; Hirao, T. Tetrahedron Lett. 1998, 3, 5213-5216 and references therein. For the uncatalyzed addition to methylpropiolate, see: (e) Kodomari, M.; Saitoh, G.; Yoshitomi, S. Bull. Soc. Chem. Jpn. 1991, 64, 3485-3487.
10. The UV-irradiation-induced addition of thiols to monosubstituted propargilyc alcohols has been also reported. See: (a) Mantione, R.; Normant, H. Bull. Soc. Chem. Fr. 1973, 2261-2265. For other additions of thiols to alkynes under radical conditions, usually giving stereoisomeric mixtures, see: (b) Kuniyasu, H.; Ogawa, A.; Sato, K.; Ryu, I.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc. 1992, 114, 5902-5903. (c) Kuniyasu, H.; Ogawa, A.; Sato, K.; Ryu, I.; Sonoda, N. Tetrahedron Lett. 1992, 33, 5525-5528. (d) Ogawa, A.; Kudo, A.; Hirao, T. Tetrahedron Lett. 1998, 3, 5213-5216 and references therein. For the uncatalyzed addition to methylpropiolate, see: (e) Kodomari, M.; Saitoh, G.; Yoshitomi, S. Bull. Soc. Chem. Jpn. 1991, 64, 3485-3487.
11. See, for instance: Lambert, J. B.; Beadle, B. M.; Kuang, K. J. Org. Chem. 1999, 64, 9241-9246.
12. For instance, the rate constant for the reaction between piperidine and methylpropiolate increases by a factor of 865 from cyclohexane to acetonitrile. See: Giese, B.; Huisgen, R. Tetrahedron Lett. 1967, 1889-1892.
13. Truce, W. E.; Heine, R. F. J. Am. Chem. Soc. 1957, 79, 5311-5313.