Tetrahedron p. 1131 - 1139 (1981)
Update date:2022-08-05
Topics:
Babin, P.
Dunogues, J.
Petraud, M.
The thermal decomposition of keto-ylides resulting from the reaction of m- and p-acetoxy benzoyl chlorides with Ph3P=CH-COOMe leads, after saponification to m- and p-phenylpropiolic acid respectively.Ortho substitution by an acyl group generally changes the orientation of the reaction.Thus o-acetoxy-, benzoyloxy- or phenylacetoxy benzoyl chlorides respectively afford: <*> and <*> (R=Me,Ph) in satisfactory yields.Saponification of the first and second ones gives:<*> (R=Me, Ph).This constitutes a new, convenient route to 3-acyl 4-hydroxy cumarins and 11-hydroxy 12H-benzoxanthene 12-one.Formation of these last products involves the carbonyl of the acyloxy-substituent and not of the acyl chloride as previously observed in these series.
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