The Journal of organic chemistry

Novel and Efficient Insertions of Carbons Carrying O-, S-, and N-Linked Substituents: Synthesis of α-Alkoxyalkyl, α-(Alkylthio) alkyl, and α-(Carbazol-9-yl) alkyl Ketones

AR Katritzky, L Xie, L Serdyuk

Index: Katritzky, Alan R.; Xie, Linghong; Serdyuk, Larisa Journal of Organic Chemistry, 1996 , vol. 61, # 21 p. 7564 - 7570

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Citation Number: 45

Abstract

A wide variety of benzotriazolyl-stabilized anions 2, obtained by the lithiation of 1-(α- alkoxyalkyl)-, 1-[α-(alkylthio) alkyl]-, and 1-[α-(carbazol-9-yl) alkyl] benzotriazoles 1, on reaction with aliphatic and aromatic aldehydes and ketones, followed by rearrangement induced by heating in the presence of zinc bromide, furnish one-carbon-homologated α- alkoxyalkyl, α-(alkylthio) alkyl, and α-(carbazol-9-yl) alkyl ketones 4 in simple one-pot ...