|Title of the article||
REACTION OF ALLYL SULFONES WITH 1-BROMOTRICYCLO[4.1.0.02,7]HEPTANE
Vasin Viktor Alekseevich, Doctor of chemical sciences, professor, head of sub-department of organic chemistry, Ogarev Mordovia State University (68 Bolshevistskaya street, Saransk, Russia), email@example.com
547.598 : 544.433.3
Background. Functionally substituted bicyclo[3.1.1]heptanes (norpinanes) are synthetic analogues of biologically active natural terpenes of pinane series. So far, these compounds have been relatively poorly studied. However, many of them are efficient building blocks in multi-step synthesis of complex polycyclic structures containing small-sized carbocycles. They are convenient models both for the special physical chemistry research and for the study of the spatial structure and conformational features of molecules with a core containing fused cyclohexane rings in position 1 and 3. In addition, it is known that the compounds exhibit a variety of biological activities. Therefore, the development of simple methods for directing the synthesis of functionally substituted bicyclo[3.1.1]heptanes and the study of their chemical properties are urgent tasks that can greatly expand the range of norpinane compounds and the derived products. Our recent research in this area shows that an effective approach for the synthesis of norpinane compounds is the bicyclobutane strategy. It is based on the selective cleavage of the central C–C bond in a relatively complex, but generally more available than norpinanes, namely, bicyclo[1.1.0]butane derivatives – tricyclo[4.1.0.02,7]heptanes. Free-radical sulfonation reactions of tricycloheptane with halogenanhydrides, thio- and selenoesters, azides, cyanides and thiocyanates of sulfoacides and, as we have recently shown, (phenyl)ethynyl- and allyl sulfones are highly prospective for the synthesis of sulfonyl-substituted norpinanes. Electron-withdrawing sulfonyl group strongly stabilizes α-carbanions generated by base treatment. It provides additional opportunities of chemical modification of norpinanes by formation of novel C–C bonds and carbon cores of organic compounds via participation of the carbanions. Note that, if necessary, sulfonyl group can be removed by elimination or replacement reactions.
allyl sulfone, radical addition, tricyclo[4.1.0.02,7]heptane, bicycle[3.1.1]heptane, norpinane, dehydrobromination, ethynyl sulfone.
1. Vasin V. A.,. Korovin D. Yu., Somov N. V. Vestnik NNGU [Billetin of NNSU]. 2013, iss. 3 (1), pp. 102–109.
Дата обновления: 24.09.2015 15:58