Phenyltelluroacrylonitriles and phenylselenoacrylonitriles as precursors of (Z)-alpha-phenylseleno-alpha,beta-unsaturated aldehydes, beta-amino-alpha-phenylselenonitriles and Diels-Alder adducts

Authors
Silveira, CC Perin, G Braga, AL Dabdoub, MJ Jacob, RG
Citation
Cc. Silveira et al., Phenyltelluroacrylonitriles and phenylselenoacrylonitriles as precursors of (Z)-alpha-phenylseleno-alpha,beta-unsaturated aldehydes, beta-amino-alpha-phenylselenonitriles and Diels-Alder adducts, TETRAHEDRON, 57(28), 2001, pp. 5953-5959
Citations number
37
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
57
Issue
28
Year of publication
2001
Pages
5953 - 5959
Database
ISI
SICI code
0040-4020(20010709)57:28<5953:PAPAPO>2.0.ZU;2-O
Abstract
Reaction of cyanomethylphosphonate with aryl selenenyl (or tellurenyl) hali des and aldehydes, under basic conditions, provides alpha -phenylseleno or alpha -phenyltelluro acrylonitriles in good yields. Reaction of the alpha - phenylseleno acrylonitriles with dienes furnishes the corresponding adducts while reaction with amines furnishes alpha -phenylseleno-beta -amino nitri les. Selective reduction of the cyano group with DIBAL-H results in the alp ha -phenylseleno-alpha,beta -unsaturated aldehydes. (C) 2001 Elsevier Scien ce Ltd. AU rights reserved.