A facile entry into a stable functionalized bis(methylene)cyclobutene system
โ Scribed by S Braverman; E.V.K Suresh Kumar; M Cherkinsky; M Sprecher; I Goldberg
- Book ID
- 104210733
- Publisher
- Elsevier Science
- Year
- 2000
- Tongue
- French
- Weight
- 170 KB
- Volume
- 41
- Category
- Article
- ISSN
- 0040-4039
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โฆ Synopsis
A parameter for the stabilization of the 3,4-bis(methylene)cyclobutene system has been identiยฎed. Appropriate functionalized derivatives, stable even in solution, have been conveniently prepared by tandem double [2,3]-sigmatropic rearrangement of conjugated dipropargylic sulfenates to diallenic disulfoxides and spontaneous cyclization of the latter. Stereochemical aspects are presented.
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A Facile Entry into the Ring System of Sativene. -Careful bromination of the diketone (I) allows the synthesis of the dibromides (II) and (III) or corresponding tribromide (IV). Their DBU-mediated dehydrobromination leads to tricyclic compounds of which (V) and (VII) have the same carbon skeleton a