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An investigation of the abnormal products from the reaction of 2‐thenyl and benzyl grignard reagents by gas chromatography.
Author(s) -
Campaigne E.,
Johnson Roger E.
Publication year - 1968
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570050215
Subject(s) - chemistry , reagent , ethylene oxide , chloride , formaldehyde , gas chromatography , magnesium , benzyl chloride , solvent , ethylene , organic chemistry , inorganic chemistry , chromatography , catalysis , polymer , copolymer
The products of the reaction of 2‐thenylmagnesium chloride (I) with a variety of reagents has been studied by gas chromatography. Carbon dioxide and ethylene oxide produced significant amounts of 5‐substituted (“ para ”) products as well as 3‐substituted (“ ortho ”) and normal addition products. Several other reagents, including acetyl chloride and formaldehyde, produced mainly “ ortho ” products along with small amounts of normal products. The dependence of product distribution on temperature, added salts and solvent character was found to correlate with the reported rates of inversion about the carbon‐magnesium bond in primary Grignard reagents. Blocking the “ ortho ” position, in 3‐methyl‐2‐thenylmagnesium chloride, increased the proportion of “ para ” product from 3 to 33%. In addition, the reactions of benzylmagnesium chloride with certain reagents were re‐examined.