We report the formation of the tricyclo[6.3.0.01\*6]undecanones x and 2, and the unusual acid-catalyzed isomerization of $, to &$. Irradiation of 1" in hexane gave z3s4 as the sole product isolated in 92% yield. Similar irradiation of ,$" gave only 2 (83%). Wolff-Kishner reduction of the new ketones
Unusual rearrangement of tricyclo[6.3.0.01,4]undecan-5-one
β Scribed by Masaki Ue; Hiroshi Tsukahara; Kazuya Kobiro; Kiyomi Kakiuchi; Yoshito Tobe; Yoshinobu Odaira
- Publisher
- Elsevier Science
- Year
- 1987
- Tongue
- French
- Weight
- 173 KB
- Volume
- 28
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
cis, truns-Tricyclo[ 6.3.0.0 124 ] undecan-B-one (3 rearranged under acidic conditions through unusual pathways to give cis,cis-tricyclo[ 6.3.0.01,5]undecan-I-one (3. The application to the c-methylene derivative of 2 afforded the angularly fused triquinane having an a-methylenecyclopentanone unit.
π SIMILAR VOLUMES
Regioselective generation of the C(2)-carbocation a of tricyc10[4.2.2.0',~]decane (1) by treatment of both corresponding epimeric alcohols 5 and 6 with BF, and trapping the rearranged tricy~lo[S.3.0.O~~~]decan-7-yl carhocation b with Et,SiH as hydride-ion donor (ionic hydrogenation) gives the corres
heptan-2-ol derivatives (4a and 4b) have been prepared. Their buffered solvolyses in anhydrous 2,2,2-trifluoroethanol were studied. Anti dinitrobenzoate 4a solvolyzes to give mainly mxylene and two trifluoroethyl ethers (5 and 6). Solvolysis of the syn mesylate 4b gives 6-rnethyl-l-(2,2,2-trifluoroe
## Abstract For Abstract see ChemInform Abstract in Full Text.
AbstractΓThe acetolysis of a tosylate with a novel tricyclic skeleton was examined. Two major products (a tosylate and an acetate) are formed and both are the result of a skeletal rearrangement. A mechanism to account for the observed products is proposed and preliminary kinetic data are reported.