Tri-n-butyl borate

Tri-n-butyl borate [688-74-4] M 230.2, b 232.4°, n 1.4092, d 0.857. The chief impurities are n-butyl alcohol and boric acid (from hydrolysis). It must be handled in a dry-box, and can readily be purified by fractional distillation, under reduced pressure. 

N-Butyl borate Butyl borate, tri- Tributoxyborane Tri-N-butoxyborane Tri-N-butyl borate... 

Tri-N-butyl borate. See Tributyl borate N,N,N-Tributyl-1-butanaminium hydroxide. See Tetra-n-butyl ammonium hydroxide N,N,N-Tributyl-1-butanaminium iodide. See Tetrabutyl ammonium iodide N,N,N-Tributyl-1-butanaminium sulfate (1 1). 

Alkylthioallyl-lithium reagents couple with allylic halides by a-a ( head-to-head ) coupling, whereas the corresponding alkylthioallyl copper compounds couple y-y ( tail-to-tail ). Allylic bromides can now be coupled with the lithium alkylthioallyl borate complex [viz. (78)] to give the 1,5-diene (79). The 9-BBN-ate complex gives a better yield and regiospecificity than the corresponding tri-n-butyl borate. 

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