SUBSTRATE ACIDITIES AND CONVERSION TIMES FOR REACTIONS OF AMIDES WITHDI-TERT-BUTYL DICARBONATE

Authors
HANSEN MM HARKNESS AR COFFEY DS BORDWELL FG ZHAO YY
Citation
Mm. Hansen et al., SUBSTRATE ACIDITIES AND CONVERSION TIMES FOR REACTIONS OF AMIDES WITHDI-TERT-BUTYL DICARBONATE, Tetrahedron letters, 36(49), 1995, pp. 8949-8952
Citations number
17
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
36
Issue
49
Year of publication
1995
Pages
8949 - 8952
Database
ISI
SICI code
0040-4039(1995)36:49<8949:SAACTF>2.0.ZU;2-W
Abstract
The conversion time for 4-dimethylaminopyridine catalyzed reaction of amides with di-tert-butyl dicarbonate varies dramatically with substra te acidity. The pK(a)'s in DMSO of some amides are determined to suppo rt correlation of reactivity with substrate acidity. Particularly acid ic substrates, such as 4-thiazolidinone, readily react with a variety of dialkyl dicarbonates. Less acidic substrates react with Boc(2)O but other dialkyl dicarbonates decompose preferentially.