Chemoselectivity in the reactions of acetylketene and acetimidoylketene: Confirmation of theoretical predictions

DM Birney, X Xu, S Ham, X Huang

Index: Birney, David M.; Xu, Xiaolian; Ham, Sihyun; Huang, Xiaomeng Journal of Organic Chemistry, 1997 , vol. 62, # 21 p. 7114 - 7120

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Citation Number: 69

Abstract

Acetylketene (1) was generated by flash pyrolysis of 2, 2, 6-trimethyl-4 H-1, 3-dioxin-4-one (6). The selectivities of 1 toward a number of representative functional groups were measured for the first time in a series of competitive trapping reactions. The trend in reactivities toward 1 follows the general order amines> alcohols≫ aldehydes≈ ketones and can be rationalized by considering both the nucleophilicity and the electrophilicity of the ...