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Thermal and Photochemical Decomposition of Dihydrooxadiazinones
Author(s) -
Fuchs B.,
Kwalwasser W. D.,
Rosenblum M.
Publication year - 1975
Publication title -
israel journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.908
H-Index - 54
eISSN - 1869-5868
pISSN - 0021-2148
DOI - 10.1002/ijch.197500016
Subject(s) - chemistry , thermal decomposition , decomposition , hydrogen atom abstraction , photochemistry , bicyclic molecule , radical , olefin fiber , alkyl , ring (chemistry) , hydrogen , organic chemistry , catalysis
3,6‐Dihydro‐1,3,4‐oxadiazin‐2‐ones may be prepared from either α‐ketols or from α‐diketones and carbethoxyhydrazine. These substances undergo thermal or photolytic (253.7 nm) decomposition to give N 2 , CO 2 and olefins. Oxadiazinones derived from medium ring α‐ketols give bicyclic hydrocarbons in addition to olefins. These are shown to be formed by decomposition of the intermediate vinyldiazene to vinyl radicals, followed by transannular hydrogen abstraction and alkyl radical addition to the olefin. A series of 5,6‐dihydro‐1,3,4‐oxadiazin‐2‐ones have also been prepared and their thermal and photolytic behavior studied.