ISSN:
0947-3440
Keywords:
[3 + 2] Cycloadditions
;
Organylseleno group transfer
;
2,3-Dihydroselenophenes
;
Polysubstituted butadienes
;
Selenium
;
Alkenes
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
(2-tert-Butylseleno)propenenitrile (12a) has been prepared and treated with dimethyl ethynedicarboxylate (3) and methyl propiolate (18) to give the 2,3-dihydroselenophenes 16 and 21, respectively. In contrast, 2-(ethylseleno)-, 2-(methylseleno)- and 2-(phenylseleno)propenenitrile (12b-d) tend to form polysubstituted butadienes 17b-d with 3 by net organoylseleno group transfer from 12b-d to C-2 of 3 following attachment of C-3 of 17 to C-3 of 3. Five-membered selenonium ylides are proposed as intermediates.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199719970315
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