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Transformation of gem ‐Dicyanoethenes by Samarium: Direct Formation of Indenes or Direct Decyanation with in Situ Disilylation
Author(s) -
Liu Yongjun,
Zhang Fuqiang,
Qi Yan,
Zhang Yongmin,
Zhang Shusheng
Publication year - 2008
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200800258
Subject(s) - chemistry , indene , moiety , samarium , intramolecular force , aryl , alkyl , in situ , stereochemistry , medicinal chemistry , organic chemistry
Intramolecular cyclization of 1,1‐diaryl‐2,2‐dicyanoethenes promoted by samarium metal in DMF in the presence of TMSCl allowed direct construction of the indene core, whereas 1‐alkyl‐1‐aryl‐2,2‐dicyanoethenes underwent intermolecular coupling cyclization and decyanation under the same conditions. Simultaneously, disilylation occurred at the amino moiety resulting from the reduction of the cyano group. However, only simple reduction of the C=C bonds is observed when a trace amount of water presented.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)