163555-07-5Relevant academic research and scientific papers
REACTIVITY OF THE ACIDS OF TRIVALENT PHOSPHORUS AND THEIR DERIVATIVES. PART III. THE =P-O- IONS IN REACTION WITH ACTIVATED ALKYL BROMIDES. ATTACK ON BROMINE vs ELECTRON TRANSFER
Dembkowski, Leszek,Rachon, Janusz
, p. 251 - 262 (2007/10/02)
The mechanism of reductive debromination in the course of the reaction of sodium dialkyl (diaryl) phosphites as well as the sodium salt of dibenzylphosphine oxide with activated alkyl bromides in THF has been investigated.Probable mechanisms namely SET and X-philic substitution are discussed.The cyclopropyl system was chosen for the study of this reaction.The results of the carried out experiments (unrearranged products, no influence of light) suggest that the cyclopropyl radical intermediate (if it is formed) does not paticipate in the product-determining step ofthe reductive debromination under the action of the =P-O- ions.Key words: Bromocyclopropanes, reductive debromination, dialkyl phosphites, diaryl phosphites, dibenzylphosphine oxide, SET, X-philic substitution.
