THE SEARCH FOR THE GAS-PHASE NEGATIVE-ION PINACOL REARRANGEMENT .2. ARYL REARRANGEMENTS

Authors
DUA S ALEXANDER MJ BOWIE JH
Citation
S. Dua et al., THE SEARCH FOR THE GAS-PHASE NEGATIVE-ION PINACOL REARRANGEMENT .2. ARYL REARRANGEMENTS, Organic mass spectrometry, 28(10), 1993, pp. 1155-1160
Citations number
28
Categorie Soggetti
Chemistry Inorganic & Nuclear",Spectroscopy
Journal title
Organic mass spectrometry → ACNP
ISSN journal
0030493X
Volume
28
Issue
10
Year of publication
1993
Pages
1155 - 1160
Database
ISI
SICI code
0030-493X(1993)28:10<1155:TSFTGN>2.0.ZU;2-J
Abstract
Deprotonated phenyl ethylene glycols, on collisional activation, lose water by a negative ion pinacol rearrangement involving phenyl migrati on. For example, deprotonated benzpinacol undergoes the following reac tion: Ph2C(OH)C(O-)Ph2 --> [PhCOCPh3 - H]- + H2O. It is proposed that this rearrangement proceeds from an eclipsed (or near eclipsed) confor mer which is stabilized d by the HO and 0- groups forming a strong int ramolecular hydrogen bond.