The generation of α-trimethylsiloxy-o-quinodimethanes induced by one-electron reduction to o-acylbenzyltributylstannanes

Tetrahedron Letters

Volumn 37, Issue 49, 1996, Pages 8891-8894

  Sano, Hiroshi ^a   Mashio, Hitoshi ^a   Nakayama, Takahiro ^a   Kosugi, Masanori ^a  

^a GUNMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

FUMARIC ACID DERIVATIVE; TETRALIN DERIVATIVE;

ARTICLE; CATALYSIS; CYCLIZATION; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0030566787     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02076-X     Document Type: Article

References (8)

1. 1. For reviews: (a) Charlton, J. L.; Alauddin, M. M. Tetrahedron, 1987, 43. 2873-2889.
2. (b) Martin, N.; Seoane, C.; Hanak, M. Org. Prep. Proced. Int. 1991, 23, 237-272.
3. 2. (a) Sano, H.; Ohtsuka, H.; Migita, T. J. Am. Chem. Soc. 1988, 110, 2014-2015.
4. (b) Sano, H.; Kawata, K.; Kosugi, M. Synlett 1993, 831-833.
5. 3. Pereyre, M.; Quintard, J-P.; Rahm, A. In Tin in Organic Synthesis, Butterworths, London, 1987; pp. 4-5.
6. 4. Corey, E. J.; Pyne, S. G. Tetrahedron Lett. 1983, 24, 2821-2824.
7. 5. 1,2-trans exo isomer: δ 0.10(s, 9H), 2.99-3.28(m, 4H), 3.70(s, 3H), 3.75(s, 3H), 5.08(d, J=8.5 Hz, 1H), 6.98-7.54(m, 4H). 1,2-cis endo isomer: δ 0.05(s, 9H), 2.83-3.28(m, 4H), 3.75(s, 6H), 5.19(d, J=3.2 Hz, 1H), 6.98-7.54(m, 4H).
8. 6. In a control experiment, it was observed that the α-trimethylsiloxy radical derived from o-tolualdehyde reacted faster with dimethyl maleate than with dimethyl fumarate.