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Synthesis, Reactions, and Properties of 2,8-Didehydronoradamantane Derivatives

✍ Scribed by Kata Mlinarić-Majerski; Goran Kragol

Publisher
John Wiley and Sons
Year
1999
Tongue
English
Weight
244 KB
Volume
1999
Category
Article
ISSN
1434-193X

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✦ Synopsis

Keywords: 2,8-Didehydronoradamantane derivatives / Cyclopropylcarbinyl / Rearrangements / Ring-opening reactions 2,8-Didehydronoradamantan-9-one (2) was readily prepared However, treatment of ketone 2 with PCl 5 proceeds through a concerted mechanism by cleavage of the C-1-C-2 bond in 2 by oxa-di-π-methane photorearrangement of brend-4-en-2one (1). Other new 9-substituted 2,8-didehydronorad-to give exo-2, 5-dichlorotricyclo[4.2.1.0 3,8 ]non-4-ene (6). The tricyclo[4.2.1.0 3,8 ]nonane skeleton was also obtained by amantanes have also been prepared from 2, [i.e. 2,8didehydronoradamantan-9-ol (3) and tosylhydrazone 4] and photochemically induced electron transfer reduction of 2 and reduction of 2 with Li/NH 3 , as well as by reduction of the ring-opening reactions have been studied. In acidic media, 2,8-didehydronoradamantan-9-ol (3) rearranges to tosylhydrazone 4 with both NaBH 3 CN and BH 3 ϫ THF. On the other hand, Wolff-Kishner reduction of 2 gave the non-the corresponding 2-substituted brend-4-ene derivatives. Exclusive formation of exo-2-substituted brend-4-enes rearranged product, 2,8-didehydronoradamantane (10). supports the formation of a bridged bicyclobutonium ion.

[a] Rudjer Bos ˇkovic ´Institute, Department of Chemistry, conc. H 2 SO 4 or HClO 4 at 90°C, brend-4-en-2-one (1) was P. O.

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