Reaction of diene-conjugated 1,3-dipolar intermediates: the formation of cycloprop[c]isoquinolines from benzonitrile o-alkenylbenzyl ylides and their rearrangements to 2-benzazepines
- 1 January 1984
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 22,p. 1531-1533
- https://doi.org/10.1039/c39840001531
Abstract
The α,β:γ,δ-unsaturated nitrile ylides (9), when generated by the 1,3-dehydrochlorination of the benzimidoyl chlorides (8) at room temperature, react by a stereospecific 1,1-cycloaddition to give the cyloprop[c]isoquinolines (10); the latter undergo two types of thermal rearrangement giving the 1H-2-benzazepines (14) when R1 or R2= H, and the 5H-2-benzazepines (17) when R1= Ph and R2= Ph or Me.Keywords
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