The photoinduced ring expansion of five membered ring nitrites: A 1,6-exo ring closure process of the intermediate 5-nitrosopentanoyl-type radical.

被引：10

作者：

Grossi, L

机构：

[1] Dipto. di Chim. Organica A. Mangini, Università di Bologna, I-40136 Bologna, Viale Risorgimento

来源：

TETRAHEDRON | 1997年 / 53卷 / 09期

关键词：

D O I：

10.1016/S0040-4020(97)00031-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The direct photolysis of cyclopentyl-type nitrites allows to detection, by EPR spectroscopy, the corresponding delta-valerolactam-1-oxyl type radical, owing to a ring expansion process as reported for steroidal 17-nitrites. For the formation of these radicals a 1,6 exo ring closure process of the intermediate 5-nitrosopenlanoyl-type radical is involved. (C) 1997 Elsevier Science Ltd.

引用

页码：3205 / 3214

页数：10

共 18 条

[1] KINETICS AND MECHANISM OF THE EXO CYCLIZATIONS OF OMEGA-FORMYLALKYL RADICALS [J].

BECKWITH, ALJ ;

HAY, BP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (07) :2674-2681

[2] KINETICS OF THE REVERSIBLE BETA-SCISSION OF THE CYCLOPENTYLOXY RADICAL [J].

BECKWITH, ALJ ;

HAY, BP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (01) :230-234

[3]

CALVERT JG, 1966, PHOTOCHEMISTRY, P450

[4]

Craig D., 1991, COMPREHENSIVE ORGANI, V7, P689, DOI DOI 10.1016/B978-0-08-052349-1.00208-0

[5]

HUCKEL W, 1941, LIEBIGS ANN CHEM, V74, P57

[6]

Huisgen R., 1952, LIEBIGS ANN CHEM, V575, P174

[7] PHOTOLYSIS OF NITRITE ESTERS IN SOLUTION .6. NITROSO DIMERS FROM ALICYCLIC NITRITES [J].

KABASAKALIAN, P ;

TOWNLEY, ER .

JOURNAL OF ORGANIC CHEMISTRY, 1962, 27 (08) :2918-&

[8] PHOTOLYSIS OF NITRITE ESTERS IN SOLUTION .7. PHOTOCHEMISTRY OF DL-BORNYL AND DL-ISOBORNYL NITRITES [J].

KABASAKALIAN, P ;

TOWNLEY, ER .

JOURNAL OF ORGANIC CHEMISTRY, 1962, 27 (10) :3562-+

[9]

MACKOR A, 1969, RECL TRAV CHIM PAY-B, V88, P1249

[10] C-NITROSO COMPOUNDS .6. ACYL-ALKYL-NITROXIDES FROM ACYL RADICALS AND NITROSO COMPOUNDS AS STUDIED BY ESR [J].

MACKOR, A ;

WAJER, TAJ ;

DEBOER, TJ .

TETRAHEDRON, 1968, 24 (04) :1623-&

← 1 2 →