Substituent control of intramolecular hydrogen bonding in formyl-protonated o-anisaldehydes: a stable ion and semiempirical MO investigation

…, GF Koser, S Subramanyam, DA Forsyth

文献索引：Laali, Kenneth K.; Koser, Gerald F.; Subramanyam, Sundar; Forsyth, David A. Journal of Organic Chemistry, 1993 , vol. 58, # 6 p. 1385 - 1392

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被引用次数: 20

摘要

o-Anisaldehyde and its 5-Br, 5-F, 5-CF3, 5-CN, 5N02, and 5-COMe derivatives are protonated at the formylgroup in 1: l SbFs-FS03H/S02 (or S02ClF) to give persistent carboxonium ions as mixtures of Z and E geometrical isomers. The cyano, nitro, and acetyl substituents are also protonated, leading to dications and additional geometrical isomers in the nitro and acetylcases. The carboxonium ions are predomiriantly in the Z, syn ...