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Contributions to the Chemistry of Boron, 128. Investigations on Substituent Exchange Reactions using 10B Labelling: Reactions of 1,3,2-Dithiaborolanes and Related Heterocycles with Boron Tribromide
Noeth, Heinrich,Staudigl, Rudolf
, p. 3011 - 3024 (2007/10/02)
The formation of the bromo derivatives from methylated dithiaza- (3) and thiadiazadiborolidines (6) and BBr3 follows the endocyclic reaction mechanism.This holds also for the substituent exchange between some 2-bromo- (9) and 2-(dialkylamino)-1,3,2-dithiaborolanes (15, 18) as demonstrated by the use of 10BBr3.An addition of BBr3 to one of the ring sulfur atoms preceeds the substitution process.Some of these adducts were isolated and the equilibrium constants of te adduct formation were determined. 3,5-Bis(diisopropylamino)-1,2,4,3,5-trithiadiborolane (22) forms alsoan S-adduct with 10BBr3 (23).The substituent exchange proceeds endocyclically while the same reaction involving the 3,5-bis(dimethylamino) derivative follows the exocyclic route.
