Double Mitsunobu reactions of cis-cycloalk-2-ene-1,4-diols and 3,4-epoxycycloalkenes: Rearrangements of allylic diazides
Özet
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.
Atıf için künye
Göksu, S., OZALP, C., Seçen, H., Sütbeyaz, Y., & SARIPINAR, E. (2004). Double Mitsunobu reactions of cis-cycloalk-2-ene-1,4-diols and 3,4-epoxycycloalkenes: Rearrangements of allylic diazides. Synthesis (Germany)(17), 2849–2854. https://doi.org/10.1055/s-2004-831258
BibTeX
@article{goksu2004-71389,
author = {Göksu, Süleyman and OZALP, C and Seçen, Hasan and Sütbeyaz, Yaşar and SARIPINAR, E},
title = {Double Mitsunobu reactions of cis-cycloalk-2-ene-1,4-diols and 3,4-epoxycycloalkenes: Rearrangements of allylic diazides},
journal = {Synthesis (Germany)},
year = {2004},
number = {17},
pages = {2849--2854},
issn = {0039-7881},
doi = {10.1055/s-2004-831258},
url = {https://akademik.atauni.edu.tr/yayinlar/71389-double-mitsunobu-reactions-of-cis-cycloalk-2-ene-14-diols-and-34}
}