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A Study of the Reactivity of Secondary Phosphanes with Radical Sources: A New Dehydrocoupling Reaction
Author(s) -
Baker Robert J.,
Hashem Emtithal
Publication year - 2010
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201000114
Subject(s) - chemistry , reactivity (psychology) , cyclohexane , stoichiometry , adduct , borane , organic chemistry , polymer chemistry , photochemistry , catalysis , medicinal chemistry , medicine , alternative medicine , pathology
The reactions of secondary phosphanes with radical sources have been investigated. A stoichiometric dehydrocoupling of Ph 2 PH with 1,1′‐azobis[cyclohexane‐1‐carbonitrile] ( VAZO ® 88 ) affords tetraphenyldiphosphane in good yields, whilst reduction of the nitrosyl function was observed upon using 2,2,6,6‐tetramethylpiperidin‐1‐oxyl (TEMPO). Dialkylphosphane–borane adducts also undergo a dehydrocoupling reaction in the presence of VAZO ® 88 to form R 4 P 2 .