Preparation of 4-substituted benzyl sulfoxylates and related chemistry

Authors
Tardif, SL Harpp, DN
Citation
Sl. Tardif et Dn. Harpp, Preparation of 4-substituted benzyl sulfoxylates and related chemistry, J ORG CHEM, 65(16), 2000, pp. 4791-4795
Citations number
21
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263 → ACNP
Volume
65
Issue
16
Year of publication
2000
Pages
4791 - 4795
Database
ISI
SICI code
0022-3263(20000811)65:16<4791:PO4BSA>2.0.ZU;2-8
Abstract
Preparation of dibenzyl sulfoxylate 7a and 4-substituted benzyl sulfoxylate s (7b, 4-NO2; 7c, 4-Cl; 7d, 4-CH3O, 7e: 4-CH3) are reported. The unexpected stability of 7b has permitted the first X-ray determination at room temper ature of a sulfoxylate. The thermal isomerization of sulfoxylates 7b-c to s ulfinates 8b-c was studied in different solvents (toluene-d(8), CDCl3, and CD3CN) and interpreted as a concerted unimolecular process following first- order kinetics.