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Nucleophilic substitution at nitrogen‐centered radicals: Reactions of diphenylphosphide ions with N , N ‐dibutyl‐ p ‐toluenesulfonamide by the S RN 1 mechanism
Author(s) -
Foray Gabriela S.,
Peñéñory Alicia B.,
Rossi Roberto A.
Publication year - 1995
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.610080507
Subject(s) - chemistry , radical , ammonia , medicinal chemistry , ion , nucleophilic substitution , nitrogen , substitution reaction , reaction mechanism , photochemistry , organic chemistry , catalysis
The photostimulated reaction of N , N ‐dibutyl‐ p ‐toluenesulfonamide with diphenylphosphide ions in liquid ammonia leads to the corresponding phosphinic amides after oxidation Inhibition experiments with p ‐dinitrobenzene and 2,2,6,6‐tetramethyl‐1‐piperidinyloxy free radical (TEMPO) and the fact that the reaction is retarded in the dark suggest that it proceeds by the S RN 1 mechanism.