Chemistry of Adamantanes by R.C. Bingham, P.R.v. Schleyer

By R.C. Bingham, P.R.v. Schleyer

Content material: fresh advancements within the chemistry of adamantane and comparable polycyclic hydrocarbons / by way of R.C. Bingham and P.V.R. Schleyer

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Starting with labeled diazomethane, 50 % of the label will be retained in the regenerated adamantyl nucleus. Treatment of the 2-hydroxy-2-adamantane carboxylic acid prepared in this manner with thionyl chloride gives the starting adamantanone labeled in the 2-position 48). The Wolff rearrangement of 5-diazo-4-homoadamantanone has similarly been employed for the preparation of ring labeled 2-adamantyl derivatives 46). Beckmann and Schmidt rearrangements of adamantanone oxime 1o4, 10%109) and adamantanone 110-ll 1), respectively, have also been studied.

Treatment of 1-bromoadamantane with AIBr3 in the presence of ethylene at -75 ~ to give 1-(/3-bromoethyl)-adamantane 202) followed by reduction 200) results in good yields of 1-ethyladamantane (Eq. (63)). Wolf-Kishner 164) or Clemensen 203) reduction of commercially available methyl adamantyl ketone provides an alternative route for the preparation of this compound. Br CH~=CH~ AlBr~-'------~_T5 2)H20 CH2CH2Br " ~ CH2CHa Conversion of the methyl ester of 1-adamantane carboxylic acid to 1-adamantyl dimethylcarbinol (66) by reaction with CH 3 Mgl followed by dehydration and subsequent hydrogenation provides a convenient route to 1-isopropyladamantane (66a) 164, 200).

Scheme 14 , Br Br Br 1 COCHN2 COOH 0 The stability and symmetry of the 8,9-dehydro-2-adamantyl cation have been investigated and comparison has been made with the cyclopropyl carbinyl cation itself 135). 1. 1 ]nonane. Photolysis of the parent diene gives 3,6dehydrohomoadamantane which, upon reaction with bromine, gives 1-bromo3-bromomethyladamantane (Eq. (44)), 36). Thermodynamic control un- (44) BrC Br doubtedly causes the rearrangement to the adamantane system during bromination. A similar rearrangement to 1-bromomethyladamantane is observed when homoadamantane itself is treated with molecular bromine 137).

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