Chemistry of Adamantanes (Topics in Current Chemistry) by R.C. Bingham, P.R.v. Schleyer

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

Content material: contemporary 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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A, CI, rn/e 135 13r, COOH, COCH 3 if it appears at all, is very weak. These functions are not lost during fragmentation, and the spectra of members of this class are quite different from one another. In each case, however, the base peak is found to arise from a fragmentation which may be represented as shown in Eq. (51). + X = C6H 5 , OH, NH 2, NHCOCH 3 47 Physical Properties C. 5 ~ (see above). Theory 17o) predicts, therefore, that all carbon bonding orbitals should be nearly pure sp 3 hydrids.

COOH (54) + 60%- 52 (55) Substitution Methods amines are also obtained from the reaction of trichloramine and aluminum chloride with adamantane 190. The 1-adamantyl cation is also trapped by 1,1-dichloroethylene 192) and 1,1,3-trichloroethylene 193) to give 1-adamantyl acetic acid (Eq. (56)) and a-chloro- l-adamantyl acetic acid (Eq. g. Eq. (58))194-196), In a similar manner, the 1-adamantyl cation adds to acetylene to give l-adamantyl acetaldehyde in addition to the AlCa, ~ CHaCH=CH hexane 2 9 (58) 4-homoadamantyl rearrangement products discussed earlier (see Scheme 11) 99).

2]octyl system 175). In this system, the effect has been attributed to a substituent induced structural perturbation. The electronegative fluorine and substituent repel each other resuiting in enhanced p-character of the endocyclic C-C bonds. The C-F bond order may, therefore, be enhanced as discussed above for the unsubstituted polycyclic fluorides 175). D. Optical Activity in Adamantane Derivatives The four bridgehead positions of adamantane are formally analogous to the four tetrahedral valences of carbon.

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