Steric effects in synthesis—steric limits to the alkylation of nitriles and carboxylic acids期刊界 All Journals 搜尽天下杂志传播学术成果专业期刊搜索期刊信息化学术搜索

Steric effects in synthesis—steric limits to the alkylation of nitriles and carboxylic acids

Authors:	John-Anthony MacPhee Jacques-Emile Dubois

Affiliation:	Institut de Topologie et de Dynamique des Systèmes de l''Université Paris VII, associé au C.N.R.S., 1, rue Guy de la Brosse, 75005 Paris, France

Abstract:	The steric limits to the alkylation of aliphatic nitriles and carboxylic acids have been investigated in some detail. For the experimental conditions considered (ionization by i-Pr₂NLi in THF followed by alkylation with RI/THF/HMPA) the most hindered nitriles R-CN and carboxylic acids R-CO₂H have the same secondary alkyi group RtBuPⁱCH-, but different tertiary. i.e. Rt-BuPrⁱEtC- or i-Pr₃C- for RCN and REt₂MeC for RCO₂H. A comparison of the relative merits of alkylation of esters, carboxylic acids, and nitriles is considered.

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