CHEMOSELECTIVE MONOALKYLATION OF 5-TRIFLUOROACETAMIDO-1-PENTANOL AND 5-ACETAMIDO-1-PENTANOL DERIVATIVES VIA N,O-BISDEPROTONATION - QUANTITATION OF EVOLVED H-2 AS A PROBE OF ANION FORMATION

Authors
HIRSCHMANN R HYNES J SPOORS PG SMITH AB
Citation
R. Hirschmann et al., CHEMOSELECTIVE MONOALKYLATION OF 5-TRIFLUOROACETAMIDO-1-PENTANOL AND 5-ACETAMIDO-1-PENTANOL DERIVATIVES VIA N,O-BISDEPROTONATION - QUANTITATION OF EVOLVED H-2 AS A PROBE OF ANION FORMATION, Tetrahedron letters, 36(14), 1995, pp. 2373-2376
Citations number
11
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
36
Issue
14
Year of publication
1995
Pages
2373 - 2376
Database
ISI
SICI code
0040-4039(1995)36:14<2373:CMO5A5>2.0.ZU;2-X
Abstract
Measurements of H-2 evolution revealed that neither 5-trifluoroacetami do-1-pentanol (1) nor 5-acetamido-1-pentanol (6) underwent complete bi sdeprotonation upon treatment with excess NaH in THF, thereby accounti ng for the unexpected course of subsequent alkylations with carbohydra te-derived triflates 2 and 7. These studies in turn led to an effectiv e protocol for generation of N,O-dianions from 1 and 6; as anticipated , the former chemoselectively furnished O-alkylation products with tri flates 2 and 15.