Structure and Dynamics of Tröger's Base and Simple Derivatives in Acidic Media

Document Type

Article

Publication Date

1-1-1984

Abstract

Tröger's base (1)1-4 was the first amine, dissymmetric solely due to pyramidal geometry about nitrogen, to be optically resolved. 5-7 Dilute acid causes racemization of 1, postulated5 to proceed through the intermediacy of iminium ion 2. Crude published racemization data5 lead to AG* of racemization in the range 18. 9-22. 6 kcal/mol. 8 This is similar to the eight-membered-ring inversion barrier of 5, 11-diacetyl-5, 6, 11, 12-tetrahydro-2, 8-dimethyldibenzo[I>1][1, 5]diazocine, 9 a reasonable model for 2. © 1984, American Chemical Society. All rights reserved.

Identifier

0000324827 (Scopus)

Publication Title

Journal of Organic Chemistry

External Full Text Location

https://doi.org/10.1021/jo00180a035

e-ISSN

15206904

ISSN

00223263

First Page

1127

Last Page

1130

Issue

6

Volume

49

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