STABILITY AND SYMMETRY OF 8,9-DEHYDRO-2-ADAMANTYL CATION

被引：101

作者：

BALDWIN, JE

FOGLESON.WD

机构：

[1] Department of Chemistry, Chemical Engineering, University of Illinois, Urbana

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1968年 / 90卷 / 16期

关键词：

D O I：

10.1021/ja01018a020

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

8,9-Dehydro-2-adamantyl 3,5-dinitrobenzoate has been synthesized and solvolyzed in 60% aqueous acetone. The activation parameters obtained were δDLH* = 25.6 keal/mol and δDLS* (25°dg) = -1.6 eu; the solvolysis product was 8,9-dehydro-2-adamantanol. The 2-deuterio- and 2-tritio-labeled 8,9-dehydro-2-adamantyl 3,5-dinitrobenzoates were solvolyzed to give isotopically scrambled products bearing labels nearly equally at carbons 2, 8, and 9. The structure of the 8,9-dehydro-2-adamantyl cation is discussed in light of these data. © 1968, American Chemical Society. All rights reserved.

引用

页码：4303 / &

共 75 条

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