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

GOKSU S., OZALP C., SECEN H., SUTBEYAZ Y., Saripinar E.

SYNTHESIS-STUTTGART, no.17, pp.2849-2854, 2004 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Publication Date: 2004
  • Doi Number: 10.1055/s-2004-831258
  • Journal Name: SYNTHESIS-STUTTGART
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.2849-2854
  • Erciyes University Affiliated: Yes

Abstract

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.