Mass spectra of 5,10‐dihydrophenarsazines, 5,10‐dihydrophenarsazine and phenophosphazine oxides, and related heterocycles
- 1 October 1970
- journal article
- Published by Wiley in Journal of Mass Spectrometry
- Vol. 3 (10) , 1287-1291
- https://doi.org/10.1002/oms.1210031008
Abstract
The electron‐impact‐induced fragmentation of eight 5,10‐dihydrophenarsazines and three 5,10‐dihydrophenarsazine oxides proceeds by loss of the exocyclic arsenic substituents to give the stable ion (II) as the base peak followed by loss of arsenic to give a carbazole species (III). The fragmentation pattern is independent of substituents at either hetero‐atom in the cases examined. Dihydrophenophosphazine oxides behave similarly but give as the base peak an ion in which the phosphoryl grouping is retained.10,11‐Dihydro‐5‐phenyl‐5H‐dibenzo[b, f][1,4]azarsepine and 2,3‐dihydro‐1,2‐diphenyl‐1H‐benz [c]azarsole fragment by different pathways. It is suggested that the ability of arsenic and phosphorus to sustain a positive charge by dπ‐pπ bonding is the dominating factor in these fragmentations.Keywords
This publication has 2 references indexed in Scilit:
- 1H NMR and ultraviolet spectra of some 5,10-dihydrophenarsazines and related compounds. Evidence for dπ-pπ interaction in arsines and arsonium compoundsJournal of Organometallic Chemistry, 1969
- Mass spectrometry of 10-chloro-5, 10-dihydrophenarsazine (adamsite) and 10-methyl-5, 10-dihydrophenarsazineJournal of Heterocyclic Chemistry, 1966