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Product‐determining factors in the grignard reactions of benzophenones. The role of the structure of alkyl groups in grignard reagents
Author(s) -
Maruyama Kazuhiro,
Matano Yoshihiro,
Katagiri Toshimasa
Publication year - 1991
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.610040806
Subject(s) - chemistry , reagent , alkyl , oxidizing agent , grignard reaction , grignard reagent , product distribution , medicinal chemistry , organic chemistry , catalysis
The mechanism of the Grignard reactions of substituted benzophenones with two kinds of alkyl Grignard reagent, n ‐C 3 H 7 MgBr, and i ‐C 3 H 7 MgBr, was investigated. In these reactions, both addition and reduction products were also generated. Based on the results of product analysis and stopped‐flow, ESR and association measurements, it was confirmed that the product distribution was governed by several factors: the oxidizing ability of benzophenones, the association ability of Grignard reagents and the structure of alkyl groups of Grignard reagents. In particular, the strength of CMg and β‐CH bonds of Grignard reagents could strongly affect the product distribution.