Trivertal

Trivertal (2,4-dimethyl-3-cyclohexenecarboxaldehyde) is an organic molecule with two chiral centers, as shown in the 2-D image. The manufactured product, a common fragrance ingredient, contains 95% of the two cis enantiomers and 5% of the trans isomers. In the fragrance industry, trivertal is called “2,4-ivy carbaldehyde”.

Commercial trivertal is likely contaminated with isomers that have the methyl groups in different positions on the ring. Thus, the melting point is depressed, and the mixture is a liquid. Purer forms are solids with a melting range of 85 to 90 ºC.

At the recent ACS National Meeting in San Diego, Guy Bertrand of the University of California, Riverside, spoke about his research group’s studies of stable cyclic (alkyl)(amino)carbenes, one of which was prepared from trivertal. The dimethylcyclohexene structure of trivertal and related compounds stabilizes the carbene, which can be used as a ligand for transition-metal catalysts.

As a proof of concept, the authors used the carbenes in gold(I) catalysts for the hydroamination of internal alkynes with secondary dialkylamines to synthesize complex quinoline derivatives in high yields. In his presentation, Bertrand discussed the mechanisms of the reactions that he reported earlier in a journal article.