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Photostimulated reactions of neopentyl halides with nucleophiles by the S RN 1 mechanism
Author(s) -
Bornancini Esteban R. N.,
Palacios Sara M.,
Peñéñory Alicia B.,
Rossi Roberto A.
Publication year - 1989
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.610020308
Subject(s) - chemistry , nucleophile , halide , ion , medicinal chemistry , photochemistry , azide , bromide , nucleophilic substitution , inorganic chemistry , organic chemistry , catalysis
The photostimulated reaction of neopentyl halides with different nucleophiles by the S RN 1 mechanism of nucleophilic substitution has been studied. Neopentyl halides do not react with carbon nucleophiles, diethylphosphite, diphenylphosphonite and azide ions, but they react with arsenide and selenide ions. The photostimulated reaction of neopentyl bromide with diphenylarsenide ions gave only the straightforward substitution product neopentyldiphenylarsine. On the other hand, the photostimulated reaction of bromobenzene with dineopentyl arsenide ions gave three arsines: dineopentylphenylarsine, neopentyldiphenylarsine and triphenylarsine. Neopentyl chloride reacts under irradiation with diphenylphosphide ions giving good yields of the substitution product.