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Prof. Dr. Hans Jüryen Bestmann and Dipl.-Chem. Martin Schmidt Synthesis of Nitriles via the Ylide Anion of Sodium Cyanotriphenylphosphoranylidenemethanide Angewandte Chemie International Edition in English 26

Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.198700791

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A convenient access to nitriles having a variety of extremely different structures is provided by the ylide anion 1, which is isolable as the sodium salt. By reaction with alkyl halides RX, 1 can be converted into cyclic α,β-unsatu-rated nitriles such as 2; the “dienyl cyanides” 3 and alkynyl cyanides R[BOND]C[TRIPLE BOND]C[BOND]CN are obtainable from 1 by reaction with aldehydes RCHO and esters RCOOR', respectively.

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