Einwirkung von Organomagnesiumverbindungen auf Bortrichlorid, Chlorschwefel, sowie auf das Chlorid und die Ester der schwefligen Säure

Organic Compounds Of Boron

“…Boron tribromide had advantages over the trichloride in that reflux conditions could be used, instead of the pressure vessel, and the reaction was more rapid (244). An ethereal solution of 3 moles of phenylmagnesium bromide [which is more reactive than the dialkylmercury ( 129 1 mole of boron trichloride was distilled; the resulting mixture was hydrolyzed (328). Probably the most successful modification involved using excess boron trifluoride, or its diethyl etherate, which was added to the Grignard reagent [alkyl Grignard reagent (191); aryl Grignard reagent (186,191)] in diethyl ether at 0°C.…”

Synthetic Approaches to Triarylboranes from 1885 to 2020

“…In an attempt to attach two arenes to the boron using Grignardr eagents, Strecker reacted an excess of phenylm agnesium bromide with BCl 3 ,b ut obtained only phenylboronic acid after aqueous work up. [51] Am ore extensive study of the reactions of aryl Grignardr eagents with the iso-butylborate ester was carried out by Kçnig and Scharrnbeck in 1915. The results were reportedi n1 930.…”

“…Furthermore, Khotinsky and Melamed characterized the phenylboronic iso‐ butyl ester and the m ‐tolylboronic iso ‐butyl ester, as well as the respective boronic acids after saponification. In an attempt to attach two arenes to the boron using Grignard reagents, Strecker reacted an excess of phenyl magnesium bromide with BCl 3 , but obtained only phenylboronic acid after aqueous work up [51] . A more extensive study of the reactions of aryl Grignard reagents with the iso ‐butylborate ester was carried out by König and Scharrnbeck in 1915.…”

Organic Sulfites.

“…The reaction of Grignard compounds with aliphatic and aromatic sulfites, similarly as with thionyl chloride, yields symmetrical sulfoxides (18,99,215). The alkyl or aryl groups introduced in the sulfoxide group originate from the Grignard reagent.…”