Stereo- and spinselectivity of primary (singlet) and secondary (triplet) Norrish type II reactions

被引：12

作者：

Griesbeck, AG

Henz, A

Kramer, W

Wamser, P

Peters, K

Peters, EM

机构：

[1] Univ Cologne, Inst Organ Chem, D-50939 Cologne, Germany

[2] Max Planck Inst Festkorperforsch, D-70569 Stuttgart, Germany

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 12期

关键词：

D O I：

10.1016/S0040-4039(98)00023-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The influence of reactive conformation and substitution pattern on the Norrish Type II reactivity and selectivity of singlet-excited phthalimides was investigated. Only the cis-diasteroisomer of the 4-tert.-butyl cyclohexylamine derivatives 1 underwent Yang cyclization. The phthaloyl leucine esters 3a and 3b both gave primarily Yang cyclization with subsequent ring expansion. As a secondary photoreaction, 3a gave Norrish II cleavage solely, wheras photolysis of the tert.-butyl ester 3b resulted in a 1:1 mixture of Norrish II cleavage and Yang cyclization product 4 and 5. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：1549 / 1552

页数：4

共 9 条

[1] C-13 MAGNETIC-RESONANCE STUDIES OF CYCLIC-COMPOUNDS .2. C-13 CHEMICAL-SHIFT PARAMETERS FOR EQUATORIAL AND AXIAL SUBSTITUENTS IN CYCLOHEXANE - SUBSTITUENTS METHYL, ETHYL, ISOPROPYL, METHOXY AND PHTHALIMIDO [J].