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Reactivity of a (Diazomethylene)phosphorane with Alkylating Agents and Lewis Acids; Synthesis of the First α‐Diazoalkylborates
Author(s) -
Sotiropoulos JeanMarc,
Baceiredo Antoine,
von Locquenghien Klaus Horchler,
Dahan Françoise,
Bertrand Guy
Publication year - 1991
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199111541
Subject(s) - diazo , chemistry , phosphorane , electrophile , lewis acids and bases , tetrahydrofuran , borane , adduct , medicinal chemistry , reactivity (psychology) , chloride , catalysis , organic chemistry , solvent , medicine , alternative medicine , pathology
An electrophilic attack at the diazo carbon atom is postulated as initiating step in the Lewis acid catalyzed decomposition of diazo compounds. Experimental detection of such primary adducts has now been accomplished with the electronically stabilized (diazomethylene)phosphorane 1 , which, for example, gives the salt 2 upon reaction with mercury( II ) chloride, and the borate 3 upon reaction with tetrahydrofuran‐borane.