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Thermal Isomerizations of Fluorinated Spiropentanes
Author(s) -
Dolbier William R. Jr.,
Sellers Simon F.,
AlSader Basil H.,
Fielder Thomas H. Jr.,
Elsheimer Seth,
Smart Bruce E.
Publication year - 1981
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.198100036
Subject(s) - chemistry , cyclobutane , thermal , photochemistry , computational chemistry , stereochemistry , organic chemistry , thermodynamics , ring (chemistry) , physics
Abstract The syntheses and thermal rearrangements and/or fragmentations of 1,1‐difluorospiropentane, 6 , 1,1,4,4‐ and 1,1,2,2‐tetrafluorospiropentanes, 7 and 8 , 1,1,2,2,4,4‐hexafluorospiropentane, 9 , and perfluorospiropentane, 10 , are described., Spiropentanes 6 and 7 undergo only rearrangement to 2,2‐difluoromethylene‐cyclobutane and 1‐(difluoromethylene)cyclobutane and to 2,2,4,4‐tetrafluoromethylenecyclobutane, respectively. Spiropentanes 8 and 9 rearrange and extrude CF 2 : competitively, while perfluorospiropentane extrudes CF 2 : exclusively. Activation parameters are presented for all processes and the mechanisms of these thermal processes are discussed in detail.