SYNTHESIS OF 2,6-DIOXABICYCLO[3.3.0]OCTANES AND 3,8-DIOXABICYCLO[4.4.0]DEC-1(6)-ENES BY ELECTROPHILIC CYCLIZATION OF 3,4-DIMETHYLENE-1,6-HEXANEDIOLS

Authors
GURSKII ME GOLOVIN SB DEKAPRILEVICH MO STRUCHKOV YT BUBNOV YN
Citation
Me. Gurskii et al., SYNTHESIS OF 2,6-DIOXABICYCLO[3.3.0]OCTANES AND 3,8-DIOXABICYCLO[4.4.0]DEC-1(6)-ENES BY ELECTROPHILIC CYCLIZATION OF 3,4-DIMETHYLENE-1,6-HEXANEDIOLS, Russian chemical bulletin, 44(7), 1995, pp. 1262-1268
Citations number
9
Categorie Soggetti
Chemistry
Journal title
Russian chemical bulletin → ACNP
ISSN journal
10665285
Volume
44
Issue
7
Year of publication
1995
Pages
1262 - 1268
Database
ISI
SICI code
1066-5285(1995)44:7<1262:SO2A3>2.0.ZU;2-O
Abstract
3,4-Dimethylene-1,6-hexane diols 2 obtained by allylboration of ketone s with 2,3-dimethylene-1,4-bis(dipropylboryl)butane 1 undergo cyclizat ion on treatment with I-2/NaHCO3 to give -cis-di(iodomethyl)-2,6-dioxa bicyclo[3.3.0]octanes (4) and/or 3,8-dioxabicyclo[4.4.0]dec-1(6)-enes (5). 4,4,9,9-Tetramethyl-3,8-dioxacyclodeca-1,6-dione (9) was synthesi zed by ozonolysis of bicyclic compound 5b. The structure of compound 5 e was confirmed by X-ray diffraction analysis.