A curious benzenoid deacylation reaction: neighbouring group participationin acylhydroxy[2.2]paracyclophanes

Authors
Braddock, DC MacGilp, ID Perry, BG
Citation
Dc. Braddock et al., A curious benzenoid deacylation reaction: neighbouring group participationin acylhydroxy[2.2]paracyclophanes, TETRAHEDR L, 42(42), 2001, pp. 7527-7529
Citations number
8
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
42
Year of publication
2001
Pages
7527 - 7529
Database
ISI
SICI code
0040-4039(20011015)42:42<7527:ACBDRN>2.0.ZU;2-B
Abstract
Attempted carbonyl reduction of acyldihydroxy[2.2]paracyclophanes with sodi um borohydride led instead to competing aromatic deacylation. The effect wa s traced to a neighbouring group participation that can be correlated with carbonyl IR stretching frequencies. Deuterium labelling studies implicate t he formal intermediacy of a solvated [2.2]paracyclophane anion ia an SEI me chanism. (C) 2001 Elsevier Science Ltd. All rights reserved.