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Volumn 54, Issue 37, 1998, Pages 11129-11140

Water accelerated Sm/TMSCl reduction system: Pinacolic coupling of aromatic carbonyl compounds and reductive dimerization cyclization of 1,1- dicyanoalkenes

(2) Wang, Lei a Zhang, Yongmin a

a ZHEJIANG UNIVERSITY (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANE; AROMATIC COMPOUND; CARBONYL DERIVATIVE; SAMARIUM; WATER;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CYCLIZATION; DIMERIZATION; PRIORITY JOURNAL; SYNTHESIS;

EID: 0032505187 PISSN: 00404020 EISSN: None Source Type: Journal
DOI: 10.1016/S0040-4020(98)00666-8 Document Type: Article

Times cited : (67)

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- Probably this result may be attributed to the difference in stability of the radical anion intermediate. A benzyl radical anion intermediate from 1,1-dicyanoalkene derived from aromatic aldehyde or ketone is stabilized by the neighboring aromatic ring, so that it is easy to form and has enough time to react with another one to form dianion and eventually to give product 5 and 6. The less stable radical anion intermediate from 4 derived from an aliphatic aldehyde or ketone is difficult to form, so that the starting material was recovered
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