Citation
Ob. Sutcliffe et al., Azafulvenium methides: new extended dipolar systems, J CHEM S P1, (15), 2001, pp. 1795-1806
Citations number
19
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
ISSN journal
14727781
→ ACNP
Issue
15
Year of publication
2001
Pages
1795 - 1806
Database
ISI
SICI code
1472-7781(2001):15<1795:AMNEDS>2.0.ZU;2-G
Abstract
The transient 1-azafulvenium methides 24, 26 and 28 generated by thermal ex
trusion 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 derivat
ives 30 electrocyclise to give novel pyrrolo[1,2-c][1,3]oxazines 32. The an
alogous 1,2-diazafulvenium methide 36 has been intercepted in [8 pi + 2 pi]
cycloadditions with electron-rich silylated acetylenes to give adducts 37-
40. This behaviour is partially explained by Frontier MO theory.