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Preparation of Imino Lactones by Electrophilic Cyclization of β,γ‐Unsaturated Hydroxamates: Formation of 3‐Cyanoprop‐2‐en‐1‐ones through Fragmentation Reactions
Author(s) -
Trabulsi Houssam,
Guillot Régis,
Rousseau Gérard
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201000376
Subject(s) - chemistry , triethylamine , electrophile , fragmentation (computing) , hexafluorophosphate , bromine , aryl , medicinal chemistry , organic chemistry , alkyl , catalysis , ionic liquid , computer science , operating system
Treatment of γ‐disubstituted β,γ‐unsaturated hydroxamates with bis(collidine)bromine(I) hexafluorophosphate led mainly to the formation of cyclic bromo imidates – the thermodynamic products. Unsaturated cyclic imidates were then obtained by treatment with triethylamine. With γ‐aryl β,γ‐unsaturated hydroxamates, the corresponding cyclic bromo imidates were also obtained. On treatment with triethylamine, however, these compounds led to the formation of 3‐cyanoprop‐2‐en‐1‐ones in good yields through fragmentation reactions.