DELTA-VALEROLACTAM DERIVATIVE OF C-60 FROM HETERO-DIELS-ALDER REACTION WITH IS(TERT-BUTYLDIMETHYLSILYLOXY)-2-AZA-1,3-BUTADIENE

Authors
OHNO M KOJIMA S SHIRAKAWA Y EGUCHI S
Citation
M. Ohno et al., DELTA-VALEROLACTAM DERIVATIVE OF C-60 FROM HETERO-DIELS-ALDER REACTION WITH IS(TERT-BUTYLDIMETHYLSILYLOXY)-2-AZA-1,3-BUTADIENE, Tetrahedron letters, 37(51), 1996, pp. 9211-9214
Citations number
22
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
51
Year of publication
1996
Pages
9211 - 9214
Database
ISI
SICI code
0040-4039(1996)37:51<9211:DDOCFH>2.0.ZU;2-Z
Abstract
The title 2-aza-1,3-diene reacted smoothly with C-60 at room temperatu re to give 2-piperidone-fused C-60 after hydrolysis. A silyoxy group o n the piperidone ring was replaced by alkoxy groups by acid-catalyzed substitution reaction with alcohols via an iminium cation intermediate . This type of reaction was applied to reduction by use of triethylsil ane to give the parent delta-valerolactam derivative of C-60. Copyrigh t (C) 1996 Elsevier Science Ltd