Journal of Organometallic Chemistry p. 225 - 235 (1996)
Update date:2022-08-03
Topics:
Brauer, David J.
Buerger, Hans
Dittmar, Thomas
Pawelke, Gottfried
Rothe, Juergen
Dimethylaminobis(trifluoromethyl)borane, (CF3)2BNMe2 (A), reacts with Grignard reagents RMgBr to yield, after hydrolysis, the dimethylamine boranes R(CF3)2B · NHMe2 (R = Me (I), Et (II), iPr (III), -CH2CH=CH2 (IV), Ph (V), pTol (VI), oTol (VII), pClC6H4 (VIII) and -C≡CH (IX)). Alkynyltrimethylstannanes Me3Sn-C≡C-R (R = Ph, nBu) add to A across the B=N double bond and yield (R-C≡C)(CF3)2B · NMe2SnMe3, the hydrolysis of which gives (Ph-C≡C)(CF3)2B · NHMe2 (X) and (nBu-C≡C)(CF3)2B · NHMe2 (XI) respectively. In contrast, mesitylmagnesiumbromide reacts with A to yield (CF3)(Mes)FB-FC=NMe2 (XII), hydrolysis of which furnishes (CF3)(Mes)FB-C(=O)NHMe2 (XIII). Of the phosphorus ylids, only Ph3P=CH2 and Ph3P=CHCH3 react with A to give the respective adducts Ph3P-CH2-(CF3)2B-NMe2 (XIV) and Ph3P-CH(CH3)-(CF3)2B-NMe2 (XV). CF3SO3CH3 alkylates XIV at the nitrogen atom to form [Ph3P-CH2-(CF3)2B-NMe3]+[CF3SO3]- (XVI). The crystal and molecular structures of XII and XIV have been determined by X-ray methods.
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