Abstract
The transient 1-azafulvenium methides 24, 26 and 28 generated by thermal extrusion of sulfur dioxide from pyrrolo[1,2-c][1,3]thiazole 2,2-dioxide 20 (R = Me), 22 and 23 undergo sigmatropic [1,8]H shifts and the 1-acyl derivatives 30 electrocyclise to give novel pyrrolo[1,2-c][1,3]oxazines 32. The analogous 1,2-diazafulvenium methide 36 has been intercepted in [8 + 2] cycloadditions with electron-rich silylated acetylenes to give adducts 37-40. This behaviour is partially explained by Frontier MO theory.
| Original language | English |
|---|---|
| Pages (from-to) | 1759-1806 |
| Number of pages | 47 |
| Journal | Journal of the Chemical Society, Perkin Transactions 1 |
| Volume | 2001 |
| Issue number | 15 |
| DOIs | |
| Publication status | Published - 2001 |
Keywords
- acids
- azafulvenium methides
- organic chemistry
- sulfur dioxide