Nucleophilic substitution at nitrogen‐centered radicals: Reactions of diphenylphosphide ions with  N , N ‐dibutyl‐ p ‐toluenesulfonamide by the  S  RN 1 mechanism | Zendy

Foray Gabriela S. | Zendy; Peñéñory Alicia B. | Zendy; Rossi Roberto A. | Zendy

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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.

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