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The reaction of 3,4-dihydro-2H-pyran with oxalyl chloride: Formation and crystal structure analysis of an unexpected bicyclic product

✍ Scribed by Bernd Schmidt; Frank Werner; Alexandra Kelling; Uwe Schilde

Publisher
Journal of Heterocyclic Chemistry
Year
2010
Tongue
English
Weight
135 KB
Volume
47
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

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3,4‐Dihydro‐2‐H‐pyran and oxalyl chloride react, depending on the conditions, to keto esters, a pyran‐3‐carboxylic acid or derivatives thereof, or to an hitherto unknown bicyclic acetal containing a vinyl chloride moiety. The structure of the latter product has been unambiguously elucidated by single‐crystal X‐ray structure analysis. A mechanism for its formation is proposed. J. Heterocyclic Chem., (2010).

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