Investigation of the Wittig reaction with electrogenerated bases: Influence of experimental conditions on the yield and stereochemistry

Authors
Bettencourt, AP Freitas, AM Montenegro, MI
Citation
Ap. Bettencourt et al., Investigation of the Wittig reaction with electrogenerated bases: Influence of experimental conditions on the yield and stereochemistry, TETRAHEDR L, 40(23), 1999, pp. 4397-4400
Citations number
11
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
23
Year of publication
1999
Pages
4397 - 4400
Database
ISI
SICI code
0040-4039(19990604)40:23<4397:IOTWRW>2.0.ZU;2-6
Abstract
The influence of experimental parameters on the yields and stereochemistry of the Wittig reaction was studied using the synthesis of stilbene initiate d by different electrogenerated bases as a model reaction. Electrolyses wer e carried out in batch cells under different conditions, including constant potential or constant current with different electrode materials and using solvents of different polarity. It is shown that proper selection of exper imental conditions in Wittig reactions allows a choice of stereoselectivity in the reactions and the optimization of yields. (C) 1999 Elsevier Science Ltd. All rights reserved.