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Stereospecific Methanol Elimination and Hidden Hydrogen Transfer in Cyclic Diesters under Electron Impact
Author(s) -
BarShai Rivka,
Bortinger Arie,
Sharvit Joseph,
Mandelbaum Asher
Publication year - 1980
Publication title -
israel journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.908
H-Index - 54
eISSN - 1869-5868
pISSN - 0021-2148
DOI - 10.1002/ijch.198000062
Subject(s) - chemistry , stereospecificity , cyclohexane , hydrogen atom , methanol , hydrogen , medicinal chemistry , elimination reaction , stereochemistry , computational chemistry , organic chemistry , catalysis , group (periodic table)
Elimination of CH 3 OH under electron impact occurs in trans ‐1,2‐ and 1,3‐dicarbomethoxycycloalkanes to a greater extent than in the cis ‐isomers. In the trans ‐diesters, one of the α‐hydrogen atoms is abstracted in the course of the elimination. In the methyl esters of cyclohexane 1,4‐dicarboxylic acids, the elimination of CH 3 OH is also specific to the trans ‐isomer, but the abstracted hydrogen atom does not originate at the α‐position. This result is explained by a stereospecific hidden hydrogen migration step, preceding the elimination.