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Photoinduced Group Transfer Radical Addition of Carbamotelluroates to Acetylenes

Authors :
Fujiwara, S.-i.
Shimizu, Y.
Shin-ike, T.
Kambe, N.
Source :
Organic Letters; June 2001, Vol. 3 Issue: 13 p2085-2088, 4p
Publication Year :
2001

Abstract

<UFIGR ID="ol016042pn00001">Te-Phenyl carbamotelluroates <BO>1</BO> add to acetylenes under irradiation of visible light to yield β-telluroacrylamides <BO>2</BO> regioselectively. This reaction would be initiated by homolytic cleavage of the carbamoyl carbon−tellurium bond, producing carbamoyl and PhTe radicals. The addition reaction proceeds via a radical chain mechanism comprising two processes:  (i) addition of carbamoyl radicals at the terminal carbon of the triple bond, giving vinylic radicals, and (ii) S<INF>H</INF>2 reaction on the Te atom caused by the attack of the vinyl radicals to <BO>1</BO>.

Details

Language :
English
ISSN :
15237060 and 15237052
Volume :
3
Issue :
13
Database :
Supplemental Index
Journal :
Organic Letters
Publication Type :
Periodical
Accession number :
ejs1161297