1,3-Benzodithiolylium tetrafluoroborate

1,3-Benzodithiolylium tetrafluoroborate may be used in the synthesis of the following:

• Dibenzotetrathiafulvalene by reacting with 1,8-diazabicyclo[5.4.0]undec-7-ene.
• Substituted arylcarbenium ions by reacting with boronic derivatives.
• α-(1,3-benzodithiol-2-ylidene) ketones and 1,3-benzodithiole by reacting with ketones.
• 2-styryl-1,3-benzodithioles by reacting with styryl-type cobaloximes.
• 2-(3-indolyl)-1,3-benzodithiolylium tetrafluoroborate by reacting with indole.
• 2-(1,3-benzodithiol-2-ylidene)-3,5-cyclohexadien-1-ones and 4-(1,3-benzodithiol-2-ylidene)-2,5-cyclohexadien-1-ones by reacting with 2,4- and 2,6-disubstituted phenols.

Preparative Method of 1,3-Benzodithiolylium tetrafluoroborate: treatment of 2-(3-methylbutoxy)-1,3-benzodithiole with Tetrafluoroboric Acid in Acetic Anhydride at 0 °C.

1,3-Benzodithiolylium tetrafluoroborate is a carbenium ionic compound. It has been synthesized by reacting 1,3-benzodithiole with trityl tetrafluoroborate. It is widely used as an α-alkylating agent for the enantioselective α-alkylation of aldehydes., The nature of adsorption of 1,3-benzodithiolylium tetrafluoroborate on various carbon nanotubes (CNTs) has been studied. 1,3-Benzodithiolylium tetrafluoroborate reacts with different nucleophilic reagents at the 2-position to form the respective 1,3-benzodithioles.

1,3-Benzodithiolylium tetrafluoroborate can be stored in the absence of moisture and light; no toxicity data is currently available; 1,3-benzodithiol-1-ium perchlorate [32283-21-9] is also known, but poses a risk of explosion.

1,3-Benzodithiolylium tetrafluoroborate is recrystallized from acetic acid or acetonitrile/ether.