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

Content material: contemporary advancements within the chemistry of adamantane and similar polycyclic hydrocarbons / via R.C. Bingham and P.V.R. Schleyer

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The syntheticutility of this reactionis therefore limitedrelative to those previouslydiscussed. F Bisnoradamantanes Favorskiiring contractionsof 1,3-dibromoadamantane-2,6-dione(55)127, 128) also providesyntheticapproachesto bisnoradamantanederivativesas illustrated in Scheme 13. 36 Bisnoradamantanes Scheme 13 O II 55 " coo KOHI~7) m. COOH COOH O ~ i2H 11 COOH More recently, other approaches to this interesting ring system have also been developed. These are illustrated in Eqs. (41) 129, ]3o) and (42) 131).

Ring Closure Reactions Although not competitive synthetically with the methods discussed above two interesting applications of ring closure reactions for the synthesis of homoadamantane derivatives have been reported. The first involves transannular cyclopropyl participation in the solvolysis of 48; acetolysis gives 3-homoadamantyl acetate as the only observed product (Eq. (32)) 112). " ~, 25~ 11a, J 14) HOAe NaOA~ OTs 48 32 (32) AcO Homoadamantanes suggests that the cyclopropane ring may not be involved to as great an extent in the rate determining step of the solvolysis as originally interpreted 112).

1]nonyl system. 1 ]nonane 121) with sodium in moist ether (Eq. (36)). 34 Noradamantanes N~ ~ l (36) molat ether CH2 0 HsC OH The structure of the product obtained from this reaction has been confirmed by X-ray analysis ~22). Details of this analysis are summarized in Table 3. Table 3. 8 Analogous transannular carbene insertion reactions have also been reported as illustrated in Eq. (37). Both 9-noradamantanone 123) and N-methyl9-aza-noradamantane 124) have been prepared in this manner. 1 ]nonane-3,7-dione to 3,7-noradamantane diol is illustrated in Eq.

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