Vinylketene-acylallene rearrangement

H Bibas, MW Wong, C Wentrup

Index: Bibas, Herve; Wong, Ming Wah; Wentrup, Curt Journal of the American Chemical Society, 1995 , vol. 117, # 37 p. 9582 - 9583

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Citation Number: 24

Abstract

As with a-oxoketene3 and imid~ ylketene,~ substitutents with an unshared pair of electrons (NH2, OH, SH, OCH3, and N (CH3) 2) lead to lower barriers while a methyl group destabilizes the four-center transition structure (Table 1). The migratory aptitudes decrease in the order N (CH3) 2> SCH3> NHCH3> SH> OCH3> NH2> OH> H> CH3. The stabilizing effect of the electron-rich substituents is readily understood in terms of the favorable ...