Preparation of unsaturated α, α-dichloro acid chlorides and intramolecular [2+ 2] cycloadditions of the α-chloroketenes reductively generated from them. Effect of …
BB Snider, M Walner
Index: Snider, Barry B.; Walner, Marleen Tetrahedron, 1989 , vol. 45, # 10 p. 3171 - 3182
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Citation Number: 24
Abstract
Reduction of unsaturated α, α-dichloracid chlorides with zinc dust in THF at reflux generates an unsaturated α-chloroketene which undergoes an intramolecular [2+ 2] cycloaddition in good yield. This reaction can be used with three carbon tethers to prepare 5-chlorobicyclo [3.2. 0] heptan-6-ones and 1-chlorobicyclo [3.1. 1] heptan-6-ones but fails with larger tethers. Unsaturated ketenes 18 and 28, with a trans-double bond, react stereospecifically to give ...
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