Cyclobutenone ethylenedithioacetals and their ready electrocyclic ring opening

Authors
Regenhardt, W Schaumann, E Moore, HW
Citation
W. Regenhardt et al., Cyclobutenone ethylenedithioacetals and their ready electrocyclic ring opening, SYNTHESIS-S, (7), 2001, pp. 1076-1080
Citations number
11
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
SYNTHESIS-STUTTGART
ISSN journal
00397881 → ACNP
Issue
7
Year of publication
2001
Pages
1076 - 1080
Database
ISI
SICI code
0039-7881(200106):7<1076:CEATRE>2.0.ZU;2-F
Abstract
Reported here is a general regiospecific synthesis of cyclobutenedione mono ethylendithioacetals which readily undergo ring opening after addition of a n organolithium reagent. The generated acyclic enols either tautomerize to the corresponding carbonyl compounds or can be trapped as silylenol ethers, which serve as electron rich dienes in Diels-Alder additions with tetracya noethylene or maleic anhydride.