Double Mitsunobu reactions of cis-cycloalk-2-ene-1,4-diols and 3,4-epoxycycloalkenes:: Rearrangements of allylic diazides

被引：11

作者：

Göksu, S

Ozalp, C

Seçen, H

Sütbeyaz, Y

Saripinar, E

机构：

[1] Ataturk Univ, Dept Chem, Fac Arts & Sci, TR-25240 Erzurum, Turkey

[2] Erciyes Univ, Dept Chem, Fac Arts & Sci, TR-38039 Kayseri, Turkey

来源：

SYNTHESIS-STUTTGART | 2004年 / 17期

关键词：

allylic diazides; Mitsunobu reaction; sigmatropic rearrangement;

D O I：

10.1055/s-2004-831258

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学]; 081704 [应用化学];

摘要：

Double Mitsunobu reactions of cis-cycloalk-2-ene-1,4-diols and 3,4-epoxycloalkenes were investigated. cis-3,5-Diazidocyclopentene, cis- 3,4-diazidocyclooctene, and cis-3,8-diazidocyclooctene were formed as sole products via the Mitsunobu reaction. cis-Cyclohex-2-ene-1,4-diol, 3,4-epoxycyclohexene and trans-2-azidocyclohex-3-en-1-ol gave a mixture of cis-3,6-diazidocyclohexene and cis- 3,4-diazidocyclohexene via a sigmatropic rearrangement. In the same manner, cis-cyclohept-2-ene-1,4-diol, 3,4-epoxycycloheptene and trans-2-azidocyclohept-3-en-1-oI gave a mixture of cis- 3,7-diazidocycloheptene and cis-3,4-diazidocycloheptene. Experimental results were explained by theoretical PM3 calculations.

引用

页码：2849 / 2854

页数：6

共 22 条

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