Boron trifluoride etherate → Nonane
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COB1[CH:8]2[CH2:9][CH2:10][CH2:11][CH:4]1[CH2:5][CH2:6][CH2:7]2.B(F)(F)F.[CH3:16]COCC.B(Cl)(Cl)Cl>O1CCCC1.CCCCC.C(OCC)C.COC(C)(C)C.CCCCCC>[CH3:16][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:4]COB1[CH:8]2[CH2:9][CH2:10][CH2:11][CH:4]1[CH2:5][CH2:6][CH2:7]2.B(F)(F)F.[CH3:16]COCC.B(Cl)(Cl)Cl>O1CCCC1.CCCCC.C(OCC)C.COC(C)(C)C.CCCCCC>[CH3:16][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:4]For example, the appropriate lithium trisubstituted-silylacetylene (2) is contacted with an equimolar amount of B-methoxy-9-borabicyclo[3.3.1]nonane (3) in a suitable anhydrous inert organic solvent such as tetrahydrofuran, hexane, t-butyl methyl ether, diethyl ether, pentane and the like with tetrahydrofuran being preferred. The reactants are typically stirred together under an inert atmosphere for a period of time ranging from 5 minutes to 48 hours at a temperature range of from -78° C. to room temperature. A temperature range of -78° C. to -40° C. and a reaction time of 1.5 hours to 5 hours are preferred. The intermediate "ate" complex thus formed is contacted with a molar excess of a suitable lewis acid such as boron trifluoride etherate, boron trichloride and the like with boron trifluoride etherate being preferred. The reactants are typically stirred together under an inert atmosphere for a period of time ranging from 5 minutes to 24 hours and at a temperature range of from -78° C. to room temperature. A temperature range of -78° C. to -40° C. and a reaction time of 15 minutes to 1 hour are preferred. The B-(2-(trisubstitutedsilyl)ethynyl)-9-boracyclo[3.3.1]nonane of formula (I) is isolated as a tetrahydrofuran complex by evaporation of the volatiles. It may be purified by crystallization from a suitable inert organic solvent such as pentane, hexane and the like. Starting materials for use in Scheme A are readily available to one of ordinary skill in the art.
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