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Thermodynamic rearrangement of the pentacyclo[5.4.0.02,6.03,10.05,9]undecane skeleton

✍ Scribed by Kata Mlinarić-Majerski; Jelena Veljković; Alan P. Marchand; Bishwajit Ganguly


Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
375 KB
Volume
54
Category
Article
ISSN
0040-4020

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✦ Synopsis


Reaction of Pentaeyclo[5.4.0.02,6.03'10.05'9]

undecmle-8,l l-dione (l) with ethanedithiol, when performed in the presence of a Lewis acid catalyst (F3B-OEt2), afforded the corresponding mono(ethylene dithioacetal), 2, along with 7,8-[(thicethano)thio]pentacyclo[6.3.0.02,6.03, lO.05,9]undecan-l 1-one mono(ethylene dithioacetal) (3). Raney nickel reduction of 2 resulted in hydrogenolysis of both the dithioacetal moiety and the cyclobutane ring in 2 and led to the formation of a complex mixture of products (7-10). In contrast to this result, Raney nickel reduction of 3 afforded a single product, i.e., 7,8-[(thioethano)thio]pentacyclo [6.3.0.02.6.03,10.05,9]tmdecane (It)in 35% yield.


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