TY - JOUR
T1 - Stereospecificity of “Retro-Diels-Alder” Fragmentation under Electron Impact
AU - Karpati, Annie
AU - Rave, Ariella
AU - Deutsch, Joseph
AU - Mandelbaum, Asher
PY - 1973/6/27
Y1 - 1973/6/27
N2 - “Retro-Diels-Alder” fragmentation under electron impact and two analogous processes which are accompanied by hydrogen migrations are highly stereospecific in three systems of diketones. The resulting ions a, b, and c are very abundant in the case of cis isomers 3, 7, and 9, but of negligible abundance in trans diketones 4, 8, and 10. The high degree of stereospecificity suggests that no rearrangement of the molecular ions to common structures precedes these fragmentation processes, and that two C,C bonds are cleaved concurrently in the course of retro-Diels-Alder fragmentation and the analogous processes in the examined systems.
AB - “Retro-Diels-Alder” fragmentation under electron impact and two analogous processes which are accompanied by hydrogen migrations are highly stereospecific in three systems of diketones. The resulting ions a, b, and c are very abundant in the case of cis isomers 3, 7, and 9, but of negligible abundance in trans diketones 4, 8, and 10. The high degree of stereospecificity suggests that no rearrangement of the molecular ions to common structures precedes these fragmentation processes, and that two C,C bonds are cleaved concurrently in the course of retro-Diels-Alder fragmentation and the analogous processes in the examined systems.
UR - http://www.scopus.com/inward/record.url?scp=33947087605&partnerID=8YFLogxK
U2 - 10.1021/ja00794a020
DO - 10.1021/ja00794a020
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AN - SCOPUS:33947087605
SN - 0002-7863
VL - 95
SP - 4244
EP - 4248
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 13
ER -