Trimethylstannane → Trimethyltin 2,5-dichlorobenzenesulfinate

Participants

Reaction Steps

A 100 ml three-necked flask, fitted with a reflux condenser and addition funnel, was flushed thoroughly with nitrogen and charged with 4.5 ml (29.4 mmoles) of a solution of trimethyltin hydride in xylene (78 volume/volume %). To this solution was added dropwise with stirring at room temperature 70 ml of a solution of 6.0 g (28.5 mmoles) of 2,5-dichlorobenzenesulfinic acid in diethyl ether. Evolution of hydrogen occurred immediately and throughout the addition which lasted one hour. The flask was cooled in ice-water, and 9.38 g of solid was collected on a filter. The solid was recrystallized from cyclohexaneligroin giving 9.28 g of trimethyltin 2,5-dichlorobenzenesulfinate, m.p. 126.3°-128.8° C. The presence of strong absorption bands at 950 and 980 cm-1, characteristic of the ##STR19## in organotin sulfinates, was observed in the infrared spectrum (KBr). The NMR spectrum showed the following characteristics: The aromatic proton ortho to the sulfinato group appeared as a multiplet centered at 765 Hz (1 proton); the remaining aromatic protons appeared as a multiplet centered at 727 Hz (2 protons); the protons of the trimethyltin group appeared as a singlet at 62 Hz flanked on either side by two satellite bands (9 protons).

Provenance & Evidence