Elimination reactions of terminal. beta.-oxy selenoxides. Synthesis of aryl and vinyl enol ethers and of furans, oxazoles, and thiazoles

M Tiecco, L Testaferri, M Tingoli…

Index: Tiecco, Marcello; Testaferri, Lorenzo; Tingoli, Marco; Marini, Francesca Journal of Organic Chemistry, 1993 , vol. 58, # 6 p. 1349 - 1354

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Citation Number: 39

Abstract

Elimination reactions of terminal selenoxides holding an alkoxy group in the 8 position, RCH- (OR) CH2SeOPh, are usually difficult and can give rise to complex reaction mixtures. We report that these reactions take place more easily whenever the oxygen atom is linked to an unsaturated group (-CH= CHR,-Ar,-CR= O,-CH= NR). These selenoxides are easily available, and the elimination reaction was employed to effect useful syntheses of both ...