A practical synthesis of novel α-dibromoalkyl- and trimethylsilylmethyl-aminoboranes and derivatives

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• 作者：H. Can Sö ; yleyici^a ; Erkan Fı ; rı ; ncı ; ^a ; Fatih Eyduran^a ; Funda Akbulat^a ; Yü ; ksel Ş ; ahin ; ^a ; ^{ysahin@adu.edu.tr}
• 关键词：Aminoborane ; Dibromomethylborane ; Dichloro(methyl)borane ; Haloboration ; Methoxyboration
• 刊名：Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy
• 出版年：2011
• 出版时间：March 2011
• 年：2011
• 卷：78
• 期：3
• 页码：1139-1142
• 全文大小：238 K

文摘

Addition of LDA to a mixture of trimethylborate and dibromomethane in THF at a temperature of −78 °C leads to the formation of dibromomethyllithium and its capture by borate ester. ClB(OMe)₂ converts the resulting borate salt to dimethoxy(dibromomethyl)borane 2. N,N-Dimethylamino(methoxy)(dibromomethyl)borane 3 and N,N-bis(dimethylamino)(dibromomethyl)borane 4 were prepared by an amination reaction between N,N-dimethylaminotrimethylsilane and dimethoxy(dibromomethyl)borane 2. To obtain dichlorotrimethylsilylmethylborane 7 not containing the α-halomethyl group, N,N-bis(dimethylamino)(trimethylsilylmethyl)borane 5 was first obtained from the reaction of ClB(NMe₂)₂ with an organolithium reagent. Dimethoxy(trimethylsilylmethyl)borane 6 was then prepared by methoxylation of compound 5. Finally, compound 7 was prepared by chlorination of 6 using BCl₃. The chemical structures of these compounds were determined using ¹³C, ¹H, ¹¹B NMR and GC/MS/MS techniques.