Boundary conditions on the partitioning of deaminatively generated benzyl cations

被引：6

作者：

Darbeau, RW ^{[1
]}

Heurtin, DJ ^{[1
]}

Siso, LM ^{[1
]}

Pease, RS ^{[1
]}

Gibble, RE ^{[1
]}

Bridges, DE ^{[1
]}

Davis, DL ^{[1
]}

Gbenekama, DG ^{[1
]}

Darbeau, NR ^{[1
]}

机构：

[1] McNeese State Univ, Dept Chem, Lake Charles, LA 70609 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2001年 / 66卷 / 08期

关键词：

D O I：

10.1021/jo001458m

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Nitrogenous entity-separated ion pairs (NESIPs) containing benzyl cations, nitrogen gas, and pivalate anions were generated via thermal deamination of N-benzyl-N-nitrosopivalamide. Some decompositions were performed in methanolic solutions saturated with selected nucleophiles: acetate, azide, or cyanide ions. Trace amounts of benzyl cyanide and tolunitriles were observed; no corresponding products were detected in the acetate and azide cases. Other decompositions were performed in the absence of traditional solvent but in the presence of the nucleophilic salts; again only poor cyanide interception of the cation was observed. The poor showing of the nucleophilic ions, when present, is discussed in the context of the lifetime of the cation, effective nucleophilicity, and cage effects in deamination.

引用

页码：2681 / 2685

页数：5

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