Reaction of vinylcarbenoids with cyclic disulfides: Formation of 1,3- insertion products as well as 1,1-insertion products

Tetrahedron Letters

Volumn 39, Issue 39, 1998, Pages 7113-7116

  Hamaguchi, Masashi ^a   Misumi, Toru ^a   Oshima, Takumi ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

Carbenes and Carbenoids; Diazo compounds; Disulfides; Rearrangements

Indexed keywords

VINYL DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CONFORMATIONAL TRANSITION; DRUG CONFORMATION; DRUG SYNTHESIS; MOLECULAR INTERACTION; STRUCTURE ANALYSIS;

EID: 0032563919     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01510-X     Document Type: Article

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25. 3) data for compounds. 7a: δ 7.71 (dd, J=6.3, 1.3 Hz, 2H), 7.57-7.20 (m, 6H), 6.67 (d, J=11.2, 1H), 4.40 (d, J=11.2, 1H), 3.85 (s, 3H), 3.72 (s, 3H). 7b: δ 8.12 (d, 2H, J = 8.6Hz), 7.80 (dd, 1H, J = 8.6, 1.3 Hz), 7.56-7.30 (m, 9H), 6.73 (d, 1H, J = 11.8Hz), 4.86 (d, 1H, J = 11.8 Hz), 3.66 (s, 3H). 7c: δ 7.57 (dd, 1H, J = 7.9, 1.3 Hz), 7.72 (td, 1H, J = 7.3, 1.3 Hz), 7.30 - 7.23 (m, 4H), 7.15 (dd, 1H, J = 7.6, 1.7 Hz), 7.10 - 7.05 (m, 3H), 6.93 - 6.76 (m, 5H), 6.55 (dd, 1H, J = 7.9, 1.0Hz), 5.79 (s, 1H), 2.38 (s, 3H), 2.32 (s, 3H). 10a: δ 7.72 (dd, 2H, J = 8.3, 1.0Hz), 7.51 (dd, 2H, J = 8.3, 1.0 Hz), 7.40 (t, 2H, J = 8.3 Hz), 7.16 (d, 1H, J= 15.5 Hz), 6.13 (d, 1H, J = 15.5 Hz), 3.84 (s, 3H), 3.65 (s, 3H). 10b: δ 8.13 (d, 2H, J = 8.9 Hz), 7.72 (dd, 2H, J = 8.3, 1.0 Hz), 7.54 (dd, 2H, J = 8.3, 1.0 Hz), 7.36-7.45 (m, 4H), 6.98 (d, 2H, J = 15.8 Hz), 6.78 (d, 2H, J = 15.8 Hz), 3.77 (s, 3H). 10c: δ 8.10(s, 1H), 8.08 (d, 2H, J = 8.6Hz), 7.80 (dd, 2H, J = 8.6, 1.3 Hz), 7.52 (dd, 2H, J = 8.6, 1.3 Hz), 7.45 (t, 2H, J = 7.9 Hz), 7.23-7.18 (m, 6H), 2.38 (s, 3H), 2.33 (s, 3H). 12: δ 8.20 (d, 2H, J = 8.6 Hz), 7.57 (d, 2H, J = 8.6 Hz), 7.09 (d, 1H, J = 15.8 Hz), 6.70 (d, 1H, J = 15.8 Hz), 3.86 (S, 3H), 3.39-3.29 (m, 2H), 2.84-2.76 (m, 2H), 2.23-1.94 (m, 2H). 13: δ 8.23 (d, 2H, J = 8.9 Hz), 7.62 (d, 2H, J = 8.9 Hz), 7.49 (d, 1H, J = 9.9 Hz), 5.82 (d, 1H, J = 9.9 Hz), 3.85 (S, 3H), 3.03-2.86 (m, 3H), 2.64-2.56 (m, 2H), 2.34-2.16 (m, 1H).