Furan, tetrahydro-, compound with borane

Hexene converted to trihexylborane by treatment with borane in tetrahydro-furan, a soln. of diazoacetone in tetrahydrofuran added during ca. 20 min. with stirring and ice-cooling at 20°, stirred 0.5 hr. at room temp., then refluxed 0.5 hr. -> 2-nonanone. Y 65%. - As in other syntheses with organoboranes, only one of the alkyl groups of the intermediate trialkylborane is constructively consumed. F. e. s. J. Hooz and S. Linke, Am. Soc. 90, 5936 (1968) synthesis of diketones s. Chem. Commun. 1969, 139 synthesis of carboxylic acid esters and nitriles s. Am. Soc. 90, 6891 deuterio compounds s. Am. Soc. 91, 6195 (1969). 

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