NITROLYSIS OF CARBOXYLIC T-BUTYL AND 1-ADAMANTYL ESTERS

Authors
STRAZZOLINI P DALLARCHE MG GIUMANINI AG
Citation
P. Strazzolini et al., NITROLYSIS OF CARBOXYLIC T-BUTYL AND 1-ADAMANTYL ESTERS, Tetrahedron letters, 39(50), 1998, pp. 9255-9258
Citations number
35
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
39
Issue
50
Year of publication
1998
Pages
9255 - 9258
Database
ISI
SICI code
0040-4039(1998)39:50<9255:NOCTA1>2.0.ZU;2-M
Abstract
A cheap, less problematic, efficient and selective reagent for the rem oval of the t-butyl and 1-adamantyl protecting groups from carboxylic esters was found to be commercial 100% HNO3 in CH2Cl2. Incidentally, 1 ,1-dimethylethyl nitrate and tricyclo[3.3.1.1(3,7)]dec-1-yl (1-adamant yl) nitrate are coproducts in a clean reaction. The procedure is in ma ny ways superior to the method employing CF3COOH. (C) 1998 Published b y Elsevier Science Ltd. All rights reserved.