A DIRECTED AMIDOHALOGENATION REACTION - AN UNUSUAL REACTION OF AZIDOFORMATES

被引：32

作者：

BERGMEIER, SC

STANCHINA, DM

机构：

[1] Division of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, The Ohio State University, Columbus, OH 43210-1291

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 26期

关键词：

D O I：

10.1016/0040-4039(95)00863-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The thermal intramolecular reaction of an azidoformate and an olefin does not provide the expected aziridine, but rather an amidohalide. This unusual product is formed via an intramolecular nitrene addition to the olefin to initially provide an aziridine. Under the reaction conditions HCl is generated from the solvent which protonates and opens the aziridine providing the observed product. This reaction proceeds with good stereoselectivity giving stereoisomeric ratios of 3:1 to 6.7:1.

引用

页码：4533 / 4536

页数：4

共 13 条

[1]

Deyrup, The Chemistry of Heterocyclic Compounds, 42, (1983)

[2]

Padwa, Woolhouse, Comprehensive Heterocyclic Chemistry, 7, (1984)

[3]

Lwowski, Carbonylnitrenes, Nitrenes, pp. 185-224, (1970)

[4]

Edwards, Acylnitrene Cyclizations, Nitrenes, pp. 225-304, (1970)

[5]

Lwowski, Acyl Azides and Nitrene, Azides and Nitrenes, pp. 205-246, (1984)

[6]

Lwowski, Nitrenes, React. Intermed., 3, pp. 305-332, (1985)

[7]

Padwa, 1,3-Dipolar Cycloaddition Chemistry, 2, pp. 277-406, (1984)

[8]

Rhouati, Bernou, Cyclisation of azidoformates, formation of aziridines, Journal of the Chemical Society, Chemical Communications, pp. 730-732, (1989)

[9]

Deroose, De Clercq, J. Org. Chem., 60, pp. 321-330, (1995)

[10]

Pearson, Bergmeier, Degan, Lin, Poon, Schkeryantz, Williams, J. Org. Chem., 55, pp. 5719-5738, (1990)

← 1 2 →