Reactivity and rearrangements of dialkyl- and diarylvinylsulfonium salts with indole-2- and pyrrole-2-carboxaldehydes

Tetrahedron

Volumn 55, Issue 35, 1999, Pages 10659-10672

  Wang, Yufeng ^a   Zhang, Weihong ^a   Colandrea, Vincent J ^a   Jimenez, Leslie S ^a  

^a RUTGERS UNIVERSITY   (United States)

Author keywords

Bicyclic heterocyclic compounds; Natural products; Rearrangements; Sulfonium salts

Indexed keywords

INDOLE DERIVATIVE; PYRROLE DERIVATIVE; SULFONE DERIVATIVE; VINYL DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; PRIORITY JOURNAL; REACTION ANALYSIS; SYNTHESIS;

EID: 0033609940     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00605-5     Document Type: Article

References (12)

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2. 2. Wang, Z.; Jimenez, L. S. Tetrahedron Lett, 1996, 37, 6049-6052.
3. 3. LaLonde, R.; Donvito, T.; Tsai, A. Can. J. Chem. 1975, 53, 1714-1725.
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7. 7. Wang, Z.; Jimenez, L. J. Org. Chem. 1996, 61, 816-818.
8. 8. Dong, W.; Jimenez, L. J. Org. Chem. 1999, 64, 2520-2523.
9. 11NOS: C, 56.75; H, 6.55; N, 8.27; found: C, 56.78; H, 6.51; N, 8.07.
10. 10. (a) Nguy, N.; Chiu, I.-C.; Kohn, H. J. Org. Chem. 1987, 52, 1649-1655.
11. (b) Chiu, I.-C.; Kohn, H. J. Org. Chem. 1983, 48, 2857-2866.
12. 11. Flushing the column with 5:95 methanol:dichloromethane produced what appeared to be the impure conjugate addition adduct shown below. This seemed to account for most of the rest of the mass balance. (equation presented)