DFT study of thermal 1,3-dipolar cycloaddition reactions between alkynyl metal(0) fischer carbene complexes and 3H-1,2-dithiole-3-thione derivatives.

DIEGO M. ANDRADA; ISRAEL FERNANADEZ; MIQUEL SOLA; ALEJANDRO M. GRANADOS

Santiago de Compostela

Congreso; Ninth Triennial Congress of World Assocition of Theorical and Cmputational Chemist; 2011

The chemistry of Fischer carbene complexes has been demonstrated to be of high importance in organic synthesis because these compounds are capable of undergoing non-conventional, high-yield transformations under mild conditions.1 Fischer carbene complexes bearing an alkenyl or alkynyl group attached to the carbene carbon atom have been reported to be excellent dienophiles, which are able to undergo different cycloadditions.2 Given the strong electron withdrawal character of the metal moiety, these compounds are better dienophiles, require shorter time and lead at better yields than their esters analogues.3 In this work we present the computational results about the thermal 1,3-dipolar cycloaddition reaction between alkynyl metal(0) Fischer carbenes (1) and 5-methyl-3H-1,2-dithiole-3-thione (2) to yield 1,3-dithiafulvene (3) within the DFT framework.4