For cyanation

The most stable Lewis structure for cyanate ion is F because the negative charge is on its oxygen... 

Pascault JP, Galy J, Mechin F (1994) Additives and modifiers for cyanate ester resins. In Hamerton 1 (ed) (1994) Chemistry and technology of cyanate ester resins. Chapman Hall, London, p 112... 

Figure 11.3 Process flow diagram for cyanation flow chemistry operations.

Rl a,p-unsat. or aliphatic, Rs = Me Scheme 2. Methodology for cyanation of ketones developed by Shibasaki and co-workers... 

Scheme 3. Cinchona alkaloid-based methodology for cyanation of ketones developed by Deng and Tian...

For an earlier report on the use of box-ligands for cyanation of aldehydes, see Corey EJ, Wang Z (1993) Tetrahedron Lett 34 4001... 

In the above calculation for cyanate, the concentration of ammonia-nitrogen was multiplied by 3 because the formula weight of CNO- is (12 + 14 + 16) or 42, which is three times 14 (the atomic weight of N, as ammonia-N).]... 

Cyanotrimethylsilane, (CH3)3SiCN. This silane is present in solution in part as the isocyanide isomer, (CH3)3SiNC. And indeed it is more useful than NaCN for cyanation of the iron complex l2 to provide 2 and 3, intermediates in a projected synthesis of tridachione. 

Isomer Distributions for Cyanations Initiated via Cation Radicals and Cyano Radicals 2... 

The lack of compounds means that generalizations cannot be advanced for cyanates in the same way that they have been developed for the thiocyanate and selenocyanate complexes. Such data as are available suggest that for 0-cyanates lie within the range for N-cyanates and that the degeneracy of the deformation mode is apparently removed for some 0-cyanates as well as for some iV-cyanates. 

Table XIX gives some shift data for cyanate compounds, where a high-field shift is seen for JV"-cyanato complexes and a downfield shift observed for EtOCN (192). Similar arguments to those used for thiocyanate complexes presumably may be also applied here.

S.C.E.) and, because diphenylacetylene is preferentially oxidized, it is likely that the aromatic compound is discharged, as for cyanation, at ca. 2 0 V. From the figures given in Table 3 it seems unlikely that localized oxidation of the triple bond is taking place even though it is the triple bond which is acetoxylated. The probable mechanism of formation of the products is indicated in Scheme 14. 

Glycosyl fluorides, already addressed as substrates for cyanations and allylations, are excellent substrates for radical-mediated C-glycosidations. As shown in Scheme 7.80, Nicolaou et al. [43] demonstrated such reactions in the coupling of 2,3,4,6-tetra-O-benzyl-D-glucopyranosyl fluoride with acrylonitrile. The reaction gave a 61% yield with an anomeric ratio of greater than 10 1 favoring the a isomer. 

Isomer distribution for cyanation of aromatic compounds has been determined in a number of cases [217-220]. The selectivity of the cyanation reaction is higher than that of the anodic acetoxylation process. This high regioselectivity has been put to good use for the preparation of 2-cyanopyrroles and 2-cyanoindoles [226] ... 

The most common strategy for laboratory-scale hydrocarbon functionalization is hydrogen atom abstraction followed by free radical recombination. This approach is exemplified by the method of Tanner for cyanation of hydrocarbon (7) to give (8 equation 3). ... 

Cyanotrimethylsilane is also a convenient source for cyanation of cyclopropanones, as exemplified by its addition to 2-(trimethylsilyl)cyclopropanone (5) in the presence of catalytic amounts of potassium cyanide and 18-crown-6. ... 

The allylation and cyanation of aldehydes and ketones are mediated by BiCl3 and BiBr3 [174, 175]. When a chiral bismuth(lll) catalyst is used for cyanation, cyanohydrins are obtained in up to 72% ee (Scheme 14.85) [175]. The Bi(OTf)3-promoted intramolecular Sakurai cyclization of homoallylic alcohols is involved as a key step in the stereoselective synthesis of polysubstituted tetrahydropyrans (Scheme 14.86) [176]. In the presence of the BiCl3-xMl binary catalyst, allyltrimethylsilane [177] and silyl enolates [178] are acylated to give aUyl ketones and /l-dikelories, respectively. 

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