2010•Journal of Heterocyclic ChemistryRequires access

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

Bernd Schmidt, W. Frank, Alexandra Kelling, Uwe Schilde

Abstract

Abstract magnified image 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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Key concepts: Oxalyl chloride, Chemistry, Pyran, Bicyclic molecule, Moiety, Chloride, Crystal structure, Orthoester