Tetrahedron

A unique 1, 2-shift selectivity in 2-hydroxypropiophenone dimethylacetals: generation of new methodologies for methyl-2-arylpropanoates and 1, 2-carbonyl …

HR Sonawane, BS Nanjundiah, DG Kulkarni, JR Ahuja

Index: Sonawane, H. R.; Nanjundiah, B. S.; Kulkarni, D. G.; Ahuja, Jaimala R. Tetrahedron, 1988 , vol. 44, # 23 p. 7319 - 7324

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Citation Number: 15

Abstract

α-Hydroxydimethylacetals I have been shown to undergo two different rearrangements involving highly selective 1, 2-shifts under mild conditions. When treated with Ph3P/CCl4, in the presence of pyridine, I were cleanly transformed via 1, 2-aryl shifts into methyl 2- arylpropanoates, an important class of anti-inflammatory agents; a pronounced substituent effect has been observed in this rearrangement. On the other hand, treatment of I with ...