Hexamethyl ditin

The ditins as of yet are insignificant commercially, although there has been interest in hexamethyl ditin [661-69-8] (Pennwalt TD-5032) as an insecticide (164,165). 

Trimethyl(trifluoromethyl)tin was first prepared via reaction of hexamethyl-ditin with excess iodotrifluoromethane under pressure at 80 °C [101]. Later this reaction was accomplished with ultraviolet light for the preparation of longer chain perfluoroalkyl analogs [102,103] (Scheme 36). 

Hexamethyl ditin (hexamethyldistannane) [661-69-8] M 327.6, m 23.5°, b 85-88°/45mm, 182°/756mm, d 1.57. Wash with H2O and extract with C H, dry by filtering through powdered Na2SO4, remove on a rotary evaporator and fractionally dist the oily residue under vacuum (b 85-... 

In Grigg s approach to hippadine (44), the biaryl carbon-carbon bond was generated via a Stille-Kelly reaction [42]. Treatment of 42 with hexamethyl ditin in the presence... 

Phot, of hexamethyl ditin in the presence of 2,6-dimethyl-y-pyrone/ Benzene... 

The stannylation and silylation of heteroaryl halides has also been studied. The stannylation of 4-iodo pyrimidine was conducted with hexamethyl and hexa-ra-butyl ditin in the presence of fluoride ion and Pd(PPh3)2(OAc)2 as catalyst. The stannylation of 5-bromopyrimidine occurred in the highest yields in the presence of the ligandless catalyst bis(7r-allylpalladium chloride).175 The silylation of bromopyridines, bromopyrimidines, and bromoquinolines also occurred after 96 h at 160 °C with Pd(PPh3)4 as catalyst in HMPT solvent.162... 

Hexamethyl- and Hexabutylditin. These ditins undergo cross-coupling with a variety of organohalides and pseudohalides (such as aryl halides, vinyl triflates, acyl chlorides, and allyl halides) in this protocol to give the correponding tin compounds. The reaction is particularly useful for preparation of organotins with labile functionalities that are not compatible with other procedures. 

The cross-coupling of ditin compounds with aryl halides was investigated already in the 1970s. Stannanes are readily available from aryl halides and hexamethyl or hexabutyl ditin (Experimental Procedure below). ... 

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