Phenylboron dibromide

A third synthetic route that has been successfully exploited in the formation of five- and six-membered heterocycles has been studied in an attempted synthesis of a borirene derivative. Reaction of phenylboron dibromide with tolan gives a mixture of products resulting from both haloboration and phenylboration 109). A Wurtz coupling reaction of the former derivative could generate a borirene derivative... 

Hexamethyldisilyl selenide in CS2 added dropwise at room temp, with stirring and exclusion of oxygen under argon to a soln. of phenylboron dibromide in CSg, and the product isolated after ca. 1 hr. triphenylboroselenine. Y 51%. M. Sdimidt and E. Kiewert, Z. Naturf. 26b, 613 (1971). 

Grignard reaction, other examples n-Butyl borate (see Phenylboronic add). r-Butylhydro-peroxide. /-Butylperbenzoate. Dibromodifluoromethane. Diethyl sulfate. Ester synthesis (see 3-Dimethylaminopropylamine). Ethoxymethyleneaniline. Ethyl chloroformate. Ethylene dibromide (entrainment). Ethylene oxide. Ethyl formate. Ethynylmagnesium bromide. Sulfur. Triethyl orthoformate. Trimethylene oxide. See also Dichloroformoxime. 

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