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Action de nucléophiles simples sur un bromoénurononitrile, précurseur et équivalent synthétique partiel d'un ynurononitrile
Author(s) -
Tronchet Jean M. J.,
Martin Olivier R.
Publication year - 1981
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.19810640828
Subject(s) - chemistry , stereospecificity , nucleophile , conjugate , stereochemistry , reactivity (psychology) , nucleophilic addition , medicinal chemistry , catalysis , organic chemistry , medicine , mathematical analysis , alternative medicine , mathematics , pathology
Reactions of Mononucleophiles with a Bromoenurononitrile, Precursor and Partial Synthetic Equivalent of an Ynurononitrile Several mononucleophiles (bases) have been reacted with one or the other of the geometrical isomers of the bromoenurononitrile 1. Depending on the nucleophile and the conditions, many different mechanistic pathways were followed, f. ex.: with OH − , stereospecific elimination from (Z) ‐ 1 leading to 2 , with N − 3 and F − , stereospecific E‐A N reactions leading from (Z) ‐ 1 to (Z) ‐ 8 and (Z) ‐ 12 respectively, with PhCH 2 SH, conjugate nucleophilic addition to 7, with Me 2 NH, conjugate nucleophilic addition followed by a S N 2 to 11 , as well as several cases of nonstereoselective, probably A N ‐E, reactions leading to 3,6,9 and 10. In spite of their diversified reactivity, bromoenurononitriles like 1 , partial synthetic equivalent of 2 , constitute useful synthetic intermediates.