TY - JOUR
T1 - Studies in Mass Spectrometry. XIII.1 Stereospecific Electron Impact Induced Fragmentation Processes in Some Tricyclic Diesters
AU - Deutsch, Joseph
AU - Mandelbaum, Asher
PY - 1970/7/1
Y1 - 1970/7/1
N2 - endo-Dimethyl esters la, 2a, 3a, and 4a undergo elimination of methanol under electron impact through a seven-centered transition state. Stereoisomeric exo diesters lb, 2b, 3b, and 4b do not appreciably eliminate methanol. Loss of methoxyl radical from the molecular ion has been observed instead. trans-Diesters lc, 2c, 3c, and 4c eliminate methanol under electron impact through a five-centered transition state. An additional stereospecific hydrogen migration accompanying retro-Diels-Alder fragmentation has been observed in the endo isomers.
AB - endo-Dimethyl esters la, 2a, 3a, and 4a undergo elimination of methanol under electron impact through a seven-centered transition state. Stereoisomeric exo diesters lb, 2b, 3b, and 4b do not appreciably eliminate methanol. Loss of methoxyl radical from the molecular ion has been observed instead. trans-Diesters lc, 2c, 3c, and 4c eliminate methanol under electron impact through a five-centered transition state. An additional stereospecific hydrogen migration accompanying retro-Diels-Alder fragmentation has been observed in the endo isomers.
UR - http://www.scopus.com/inward/record.url?scp=18444385474&partnerID=8YFLogxK
U2 - 10.1021/ja00717a025
DO - 10.1021/ja00717a025
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AN - SCOPUS:18444385474
SN - 0002-7863
VL - 92
SP - 4288
EP - 4291
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 14
ER -