Insight into the addition reactions of stannylenoid H2SnLiF with ethylene.

Abstract

Tetrylenoids, R2EXM (E = Si, Ge, and Sn; X = electronegative group; M = alkali metal), have electrophilic and nucleophilic properties just like carbenoid. As the products of carbenoid compounds with olefins, the cyclopropane fraction has been found to be biologically active in many natural and artificial compounds. Can carbenoid analogues of stannylenoid facilitate similar cyclopropanation reactions? Addition reaction of the stannylenoid compound H2SnLiF with ethylene was investigated using density function theory (DFT) at the M062X/def2-TZVP level. The single-point energy calculations were performed on the basis of QCISD/def2-TZVP level. Two possible pathways were found for the addition reaction of H2SnLiF (R1) with ethylene (R2). The most favorable path is the two successive reactions of H2SnLiF and ethylene through the ternary ring product c-H2Sn(CH2)2 (P1) and then the formation of the five-membered ring product (P2). Solvation-related studies have shown that addition reactions are more likely to occur in the presence of THF solvents. This work provides theoretical support for the reactions of stannylenoid with olefins.