Premium
Intermolecular methyl transfer on pyrolysis of carpronium chloride
Author(s) -
Ohya Kazumi,
Yotsui Yasuhiko,
Sano Mitsuji
Publication year - 1979
Publication title -
organic mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 0030-493X
DOI - 10.1002/oms.1210140202
Subject(s) - chemistry , pyrolysis , demethylation , methyl group , deuterium , chloride , intermolecular force , mass spectrometry , medicinal chemistry , mass spectrum , organic chemistry , ion , photochemistry , inorganic chemistry , molecule , group (periodic table) , chromatography , biochemistry , gene expression , physics , quantum mechanics , dna methylation , gene
The methyl transfer occurring in the production of methyl N,N ‐dimethyl‐γ‐aminobutyrate by pyrolysis of carpronium chloride was examined by means of pyrolysis gas chromatography mass spectrometry with the aid of some deuterated compounds. The mass spectra of methyl N,N ‐dimethyl‐γ‐aminobutyrate, produced from deuterated derivatives of carpronium chloride, showed inter alia , characteristic molecular ion peaks which indicated that the methyl of the trimethylammonium group transfers and displaces the methyl of the carbomethoxy group of the tertiary amino compound. The results show that an intermolecular methyl transfer occurs in part on pyrolysis of carpronium chloride, to form methyl N,N ‐dimethyl‐γ‐aminobutyrate in which the methyl oxygen is replaced by a methyl from the nitrogen of the original compound. The mechanism presented involves the bimolecular reaction between zwitterionic intermediates formed by ionic O ‐demethylation of carpronium chloride.