Synthesis of 4‐Bromocubane‐1‐carbaldehyde.

Abstract

Synthesis of 4-Bromocubane-1-carbaldehyde. -(SHASTIN*, A. V.; ZAKHAROV, V. V.; BUGAEVA, G. P.; EREMENKO, L. T.; ROMANOVA, L. B.; LAGODZINSKAYA, G. V.; ALEKSANDROV, G. G.; EREMENKO, I. L.; Russ.

Convenient preparative synthesis of pentacyclo[5.3.0.02,5.03,9.04,8]decane (C 2-Bishomocubane)

“…The system CCl 4 -PPh 3 is known to perform well in reactions of chlorodehydroxylation of alcohols prone to isomerization or decomposition under the common conditions of the replacement of the hydroxy group by halogen at the secondary carbon atom [8,9]. With compound III the reaction proceeded sufficiently fast (4-6 h) affording chloroine-substituted ketal IV (yield no less than 90%), and the treatment of the reaction mixture with the finely ground lithium iodide forming with the triphenylphosphine oxide a complex insoluble in ether made it possible to get rid completely of the triphenylphosphine oxide in the reaction product.…”

“…The synthesis of pentacyclo [5.3.0.0 2,5 .0 3,9 .0 4,8 ]-decane-6,10-dione 6-ethyleneketal (II), bifunctional derivative of C 2 -bishomocubane, one among the most promising representatives of the homocubane series, was performed in five stages [4] starting with cyclopentanone. The final stage in this procedure consisted in the photocyclization of tricyclo[5.2.1.0 2,6 ]deca-4,8-diene-3,10-dione 10-ethyl-eneketal (I).…”