Development of Generation Method of Unstable Chemical Species Using Characteristics of Heteroatom Compounds

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We have investigated the new generation method of unstable chemical species by the use of the characteristics of heteroatom compounds and the utilization of these species in organic synthesis. In the course of our study, we found that nitre or nitrenoid species were generated efficiently by the reduction of aromatic nitro compounds with carbon monoxide in the presence of a catalytic amount of selenium. N-Heterocyclic compounds such as indols and 4(3H)-quinazolinones were synthesized by the selenium-catalyzed reaction of 0-nitrostyrenes and 0-nitrobenzoylamides with carbon monoxide in moderate to good yields. In addition, we have also developed the new generation method of vinyl radical via the thermal decomposition of 1,2,3-selenadiazoles. When 1,2,3-selenadiazoles were treated with olefins under thermal condition, the addition of vinyl radical generated in situ to carbon-carbon double bond and followed by intramoleculer cyclization proceeded efficiently to give the corresponding dihydroselenophenes in moderated to good yields. This reaction was hardly promoted by the addition of a catalytic amount of organostannyl radical.