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4-(Phenylsulfanyl)tricyclo[3.1.0.02,6]hexan-3-one: Synthesis, Alkylation, and Base-Induced Dimerisation

✍ Scribed by Ulrike Kunz; Stefan Krimm; Thomas Fischer; Thomas Kottke; Dietmar Stalke; Manfred Christl

Publisher
John Wiley and Sons
Year
1998
Tongue
English
Weight
216 KB
Volume
1998
Category
Article
ISSN
1434-193X

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✦ Synopsis

3-(Phenylsulfanyl)benzvalene ( 6) was prepared by de-methyl iodide and 1,3-diiodopropane afforded the alkyl derivatives 9 and 10, respectively, of 7. In the absence of an hydrochlorination from the adduct 5 of phenylsulfenyl chloride to benzvalene (4) with potassium tert-butoxide. An active alkylating agent, the reaction of 7 with potassium hydride gave rise to the bicyclohexyltricyclohexanes 11 autoxidation transformed 6 readily to the tricyclo-[3.1.0.0 2,6 ]hexanone 7, which was converted into its 4-being dimers of 7. Presumably, this process is initiated by the rearrangement of 7 to the bicyclohexenone 13 and completed deuterio derivative [4-D]-7 under mild conditions. The treatment of 7 with potassium hydride in the presence of by a Michael addition of 7 to 13.

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racemization (k) are determined to be ca. 71 kJ/mol and ca. 3.8 x lop3 s -' (39"C), respectively. The energy of racemization found for 1,l for '-binaphthyl (R)and (S)-lb derivatives['']. is comparable The steric to those hindrance caused by two substituents should be smaller in lb than in l a , sinc