The hydrocyanation of free and polymer-bound benzoquinone

Perry G.J. and Sutherland M.D. (1982) The hydrocyanation of free and polymer-bound benzoquinone. Tetrahedron, 38 10: 1471-1476. doi:10.1016/0040-4020(82)80233-0

Author Perry G.J.
Sutherland M.D.
Title The hydrocyanation of free and polymer-bound benzoquinone
Journal name Tetrahedron   Check publisher's open access policy
ISSN 0040-4020
Publication date 1982-01-01
Sub-type Article (original research)
DOI 10.1016/0040-4020(82)80233-0
Volume 38
Issue 10
Start page 1471
End page 1476
Total pages 6
Language eng
Subject 1303 Specialist Studies in Education
1605 Policy and Administration
3002 Drug Discovery
Abstract The polymer-bound quinone 2 has been prepared and used in column form with organic solvents for the convenient preparation of other quinones. In contrast to the solution reaction hydrocyanation of this quinone by the Thiele-Meisenheimer reaction did not yield a useful proportion of polymer-bound dicyanohydroquinone but instead gave a mixture of products including much monocyanohydroquinone. Helferich and Bodenbender's 2,3-dicyanocyclohexan-1, 4-dione is in fact wholly the di-enol and is a likely intermediate in the hydrocyanation of benzoquinone, being oxidised by the latter to 2,3-dicyanocyclohex-2-ene-1, 4-dione which tautomerises to the observed product, 2,3-dicyanohydroquinone. A lower accessibility to polymer-bound reactants as compared with those in solution is implied by these results.
Q-Index Code C1
Q-Index Status Provisional Code
Institutional Status Unknown

Document type: Journal Article
Sub-type: Article (original research)
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Created: Tue, 05 Jul 2016, 11:50:34 EST by System User