Synthesis 2002(16): 2373-2378
DOI: 10.1055/s-2002-35264
PAPER
© Georg Thieme Verlag Stuttgart · New York

One-Pot and Stereospecific Synthesis of cis-1,2-Diazides via Mitsunobu Reaction­ of Epoxides

Süleyman Göksu, Hasan Seçen*, Yasar Sütbeyaz*
Department of Chemistry, Faculty of Arts and Sciences, Atatürk University, 25240 Erzurum, Turkey
Fax: +90(442)2360948; e-Mail: hsecen@atauni.edu.tr;
Further Information

Publication History

Received 1 July 2002
Publication Date:
04 November 2002 (online)

Abstract

Mitsunobu reaction of epoxides using hydrazoic acid, diethylazodicarboxylate, and triphenylphosphine as reagents gave the corresponding cis-1,2-diazides in moderate yield. Application of similar reaction conditions to trans-diols furnished the corresponding trans-1,2-diazides.

16

See ref. 10b especially pp 375.

27

See ref. 22 pp 160.

31

See ref. 22 pp 161.

34

See Ref. 17 pp. 446.