Next Article in Journal
Photooxygenation of Nimonol, a Tetranortriterpenoid from Azadirachta indica. A. Juss.
Previous Article in Journal
Synthesis of Heterocyclic Skeletons by the Reaction of N1-(2-Cyanophenyl)-benzimidoyl Chloride with Thioamides
Article Menu

Export Article

Open AccessArticle
Molecules 2002, 7(2), 104-111; doi:10.3390/70200104

An Investigation of the Reactions of Substituted Homoallylic Alcohols with Various Oxidation Reagents

1
Department of Chemistry, Fõrat University, Faculty of Science and Arts, 23169, Elazõğ, Turkey
2
Department of Chemistry, Uludağ University, Faculty of Science and Arts, Bursa, Turkey
*
Author to whom correspondence should be addressed.
Received: 19 June 2001 / Revised: 6 November 2001 / Accepted: 26 January 2002 / Published: 28 February 2002
View Full-Text   |   Download PDF [98 KB, uploaded 18 June 2014]   |  

Abstract

Substituted homoallylic alcohols have been synthesised both by [2,3]-Wittig rearrangement of unsymmetrical bis-allylic ethers and reaction of alkenyl chloromethyl oxiranes with Mg/THF. These substrates were then oxidized using four different oxidants. When the substituted homoallylic alcohols were oxidized with pyridinium chlorochromate or zinc chlorochromate nonahydrate the corresponding carbonyl compounds were produced. The same substrates formed the corresponding allylic oxidation products together with epoxidation products when oxidized with t-BuOOH. When and t-BuOOH and catalytic amounts of OsO4 were used the allylic oxidation reaction was prevented and the only products formed were those in which the substituted double bond was epoxidized.
Keywords: Substituted homoallylic alcohols; oxidation reagents; osmium tetroxide; t-butyl hydroperoxide Substituted homoallylic alcohols; oxidation reagents; osmium tetroxide; t-butyl hydroperoxide
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

Scifeed alert for new publications

Never miss any articles matching your research from any publisher
  • Get alerts for new papers matching your research
  • Find out the new papers from selected authors
  • Updated daily for 49'000+ journals and 6000+ publishers
  • Define your Scifeed now

SciFeed Share & Cite This Article

MDPI and ACS Style

Servi, S.; Acar, A. An Investigation of the Reactions of Substituted Homoallylic Alcohols with Various Oxidation Reagents. Molecules 2002, 7, 104-111.

Show more citation formats Show less citations formats

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top