(Nitroaryl) sulfinyl-substituted allenes. Novel and convenient propargyl alcohol synthons in 4+ 2 cycloaddition chemistry

…, WH Bullock, BH Norman, J Perumattam

Index: Padwa, Albert; Bullock, William H.; Norman, Bryan H.; Perumattam, John Journal of Organic Chemistry, 1991 , vol. 56, # 13 p. 4252 - 4259

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Citation Number: 44

Abstract

(Nitroary1) sulfiiyl-substituted allenes are conveniently prepared by treating propargyl alcohol or methyl 3-hydroxy-2-butynoate with a (nitroary1) sulfenyl chloride and triethylamine. These activated allenes undergo 4+ 2 cycloaddition the C1C2%-bond. The initially formed allylic sulfoxide readily undergoes a 2, 3-aigmatropic rearrangement to produce a stable sulfenate eater that ie eanily cleaved with thiophilic magenta. The ...