Premium
Effects of annulation on the mass spectral behaviour of bicyclo[4.3.0]‐3‐nonene derivatives: Alkoxy esters
Author(s) -
Tureček F.,
Hanuš V.
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.1210140804
Subject(s) - annulation , chemistry , alkoxy group , alcohol , mass spectrum , fragmentation (computing) , bicyclic molecule , ether , benzene , medicinal chemistry , deuterium , stereochemistry , organic chemistry , ion , alkyl , catalysis , physics , quantum mechanics , computer science , operating system
Fragmentation of ethyl(18‐alkoxybicyclo[4.3.0]‐3‐nonene‐7‐carboxylates) was found to depend on the annulation of the rings. Following ionization, the cis ‐annulated isomers lose alcohol and benzene, while the trans ‐isomers fragment by other reaction paths. The regiospecificity of alcohol elimination from both the ester and the ether groups was determined by using deuterium‐labelled analogues. A mechanism is discussed which rationalizes the differences observed in the spectra of the annulation isomers.