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Facile and convenient synthesis of B-amino-9-borabicyclo[3.3.1]nonanes. Aminoboration of lsocyanates

✍ Scribed by Bakthan Singaram

Publisher: John Wiley and Sons
Year: 1992
Tongue: English
Weight: 441 KB
Volume: 3
Category: Article
ISSN: 1042-7163
DOI: 10.1002/hc.520030309

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✦ Synopsis

The reaction of 9-borabicyclo[3.3.l]i~onane with aliphatic and aromatic primary and secondary antines in tetrahydrofuran (THF) at 65°C proceeds rapidly and quantitatively with evolution of hydrogen and the foniuztion of the corresponding B-amino-9-borabicyclo[3.3. l } nonane (B-amino-9-BBN). Simple evaporation of THF frowi the reaction mixture gives the Bamino-9-BBN derivatives in high yield and purity. These B-amino-9-BBN derivatives are reactive towards alkyl and aryl isocyanates. Consequently, the aininoboration of various isocyanates has been studied using B-pheiiylaniino-9-BBN. Thus, two equivalents of isocyanates react with one equivalent of B-phenylaiiiino-9-BBN to afford, following the hydrolysis of the intermediate with ethanolaiitine, N, N'-disubstituted-N -(phenylaantido)u r e a in excellent yields. A plausible rrlechanisiit for this aritinoboration reaction of isocyanates is also presented,

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