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Stereospecific hydrogen migration in retro ‐diels‐alder fragmentation of some polycyclic imides
Author(s) -
Lesman Thila,
Deutsch Joseph
Publication year - 1973
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.1210071204
Subject(s) - fragmentation (computing) , moiety , stereospecificity , hydrogen atom , chemistry , hydrogen , diene , imide , stereochemistry , medicinal chemistry , photochemistry , organic chemistry , catalysis , alkyl , natural rubber , computer science , operating system
A stereospecific ‘ retro ‐Diels‐Alder’ fragmentation followed by hydrogen migration was found in the mass spectra of imides and phenyl imides of decahydroindacene 4,5‐dicarboxylic acid. The fragmentation involves a one hydrogen atom rearrangement when the charge is retained on the diene moiety and double hydrogen rearrangement when the charge is on the dienophilic moiety.