a) (CH30)z P-CH=C-CHzBr (3) NaH/THF b) 2N HCI C) (Bu~N) OH tolueneiH20 H 4a ('exo')
Synthesis of (4.5.5.5]fenestrane and a [4.4.5.5]fenestrane derivative
β Scribed by William G. Dauben; Daniel M. Walker
- Publisher
- Elsevier Science
- Year
- 1982
- Tongue
- French
- Weight
- 230 KB
- Volume
- 23
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
The synthesis of tetracyclo15.4.1.0 4~12.0g~121dodecan-6-one JJ via an intramolecular photocycloadditlon, its reduction to the hydrocarbon Q, and its ring-contraction to tetracyclo-[4 4 1 03*11.09JI . . . lundecane derivative g is described. The hydrocarbon tetracyclo13.3.1.03~g.07~glnonane ,I, known as [4.4.4.4lfenestrane, or simply windowpane, has been the subject of several recent discussions' and synthetic studies.* The synthetic work has resulted in the synthesis of 15.5.
π SIMILAR VOLUMES
The efficient synthesis of all-cis-[5.5.5.5]fenestrane (2) from the readily available intermediate 3 allowed the electron-diffraction analysis of 2. This structure analysis revealed long C-C bonds in the central C(C), fragment and a twist-envelope conformation for the four cyclopentane substructures
Pd-catalyzed reaction of 3-acetoxy-8-butenyl-@ and 8-but-3-inyl-bicyclo[3.3.0]oct-1 -ene (11) with CO in CH3COOf-I lead via double annulation to alLcis[5555]fenestranes. Common feature of a variety of recently developed methods for synthesis of diquinanes from openchain compounds is the transition m