HYDROLYSIS OF 1,4,6-TRIOXASPIRO[4.5]DECANES TO DELTA-LACTONES USING 2,3-DICHLORO-5,6-DICYANOBENZOQUINONE IN AQUEOUS ACETONE

Authors
VASUDEVAN S WATT DS
Citation
S. Vasudevan et Ds. Watt, HYDROLYSIS OF 1,4,6-TRIOXASPIRO[4.5]DECANES TO DELTA-LACTONES USING 2,3-DICHLORO-5,6-DICYANOBENZOQUINONE IN AQUEOUS ACETONE, Journal of organic chemistry, 59(2), 1994, pp. 361-364
Citations number
24
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
59
Issue
2
Year of publication
1994
Pages
361 - 364
Database
ISI
SICI code
0022-3263(1994)59:2<361:HO1TDU>2.0.ZU;2-I
Abstract
A selective hydrolysis of 1,4,6-trioxaspiro[4.5]decane orthoesters by 2,3-dichloro-5,6-dicyanoquinone (DDQ) in aqueous acetone in the presen ce of other acid-sensitive ketals is suggested to involve the formatio n of a charge-transfer complex followed by hydrolysis. A hydride-trans fer mechanism for this oxidation was excluded.