Cyanoborane

Using a procedure similar to the synthesis of amine boranes, a series of amine cyanoboranes where the amine = (CH3)3N, (CH3)2NH, (CH3)NH2, C3H3N, or (CgH3)NH2 have been prepared as shown in equation 4 (11). 

Trimethyl amine carboxyborane can be synthesized from the cyanoborane precursor [30353-61-8] according to equations 5 and 6 (12). 

Cyanoborane oligomer, 0393 /V-Cyano-2-bromocthylcyclohcxy laminc. 3178 Cyanocyclopropane, 1463 Cyanodiazoacetyl azide, 1346... 

A second candidate for dihydrogen bonding of B-H- H-N is 2 -deoxycyti-dine-N(3)-cyanoborane, the molecular structure of which is depicted in Figure 5.10. The BH- HN distance in this molecule is 2.05 A, smaller than the vau der Waals sum, and the Mulliken charges at the hydrogen atoms in the BH- -HN pair are opposite. 

Figure 5.10 Single-crystal x-ray structure of 2 -deoxycytidine-N(3)-cyanoborane with a BH- HN(4) distance of 2.05 A. (Reproduced with permission from ref. 14.)...

See Sodium chlorate Cyanoborane oligomer See related BORANES, cyano compounds... 

Cyanoborane oligomer, 0392 lV-Cyano-2-bromoethylbutylamine, 2842 lV-Cyano-2-bromoethylcyclohexylamine, 3172 Cyanodiazoacetyl azide, 1342 5-Cyano-4-diazo-477-1,2,3-triazole, 1341 Cyanodimethylarsine, 1195... 

Cyanoborane oligomer, 0392 Cyanocyclopropane, 1459 Cyanodiazoacetyl azide, 1342 2-Cyanoethanol (3-Hydroxypropanenitrile), 1177 Cyanoform, 1379... 

Palladium-catalysed addition of cyanoboranes Y2B-CN, [Y2 = ((-Pr)2NCH2CII2N ( -Pr)2], to alkynes, such as Ar-C=CR, produces the Z-configured a,/S-unsaturated /i-boryl nitriles ArC(CN)=C(BY2)R with good regio- and stereo-selectivity.81... 

A new method for the addition of cyanoboranes to alkynes was developed (Equation (51)).264 The B-Pd-CN intermediate obtained by oxidative addition was trapped in situ by a internal triple bond with high stereo- and... 

A separate series of closo-carboranes, isoelectronic with the BnH2 dianions and the neutral QB 2H compounds, consists of the monocarbon anions CB iH (Table 5-3). The preparative routes to these species vary widely, but a commonly used method for incorporating a single carbon atom into a borane cage involves the conversion of cyanoboranes to amino derivatives the cyano carbon atom satisfies its valence requirements via absorption into the cluster framework. 

Cyanoborohydride and its modified reagents have been used for reductive dehalogenations. Thus, the combination of sodium or tetrabutylammonium cyanoborohydride, sodium or potassium 9-cyano-9-hydro-9-borabicyclo[3.3.1]nonanate [9-BBNCN] (2) or polymeric cyanoborane (3) in HMPA furnishes an efficient and mild system for the reduction of alkyl halides. The reagents are selective in that other functional groups, including ester, carboxylic acid, amide, cyano, alkene, nitro, sulfone, ketone, aldehyde and epoxide, are essentially inert under the reduction conditions thus, the reduction procedure is attractive for synthetic schemes which demand minimum damage to sensitive portions of the molecule. 

Cyanoborane adducts of morpholine and dimethylamine undergo the following hydrolysis reaction ... 

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