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Carbene elimination from ionized methanoannulenes
Author(s) -
Wesdemiotis Ch.,
Schwarz H.,
Budzikiewicz H.,
Vogel E.
Publication year - 1981
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.1210160209
Subject(s) - annulene , fragmentation (computing) , naphthalene , carbene , ion , chemistry , ionization , photochemistry , computational chemistry , medicinal chemistry , organic chemistry , computer science , catalysis , operating system
Evidence is produced to demonstrate that loss of CH 2 from methanoannulenes is a multistep process initiated by a rearrangement yielding (at least in the case of 1,6‐methano[10]annulene) the isomeric benzocycloheptenes. Loss of CF 2 , however, apparently is a cheletropic reaction accompanied by rearomatization, thus giving rise to the formation of the molecular ion of naphthalene in the case of 11,11‐difluoro‐1,6‐methano[10]annulene. These findings present further evidence for the parallel behaviour of the bridged annulenes regarding thermal transformations and fragmentation of the molecular ions.