ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Reactions of Mononucleophiles with a Bromoenurononitrile, Precursor and Partial Synthetic Equivalent of an YnurononitrileSeveral 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-AN reactions leading from (Z)-1 to (Z)-8 and (Z)-12 respectively, with PhCH2SH, conjugate nucleophilic addition to 7, with Me2NH, conjugate nucleophilic addition followed by a SN2 to 11, as well as several cases of nonstereoselective, probably AN-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.
Additional Material:
2 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19810640828
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