29417-19-4Relevant academic research and scientific papers
Synthesis of Cyclic Ethers via Bromine Assisted Epoxide Ring Expansion
Davies, Stephen G.,Polywka, Mario E. C.,Thomas, Susan E.
, p. 1277 - 1282 (2007/10/02)
Neighbouring group participation by epoxide oxygen in the opening of bromonium ions results in the stereoselective synthesis of cyclic ethers. 9-Oxabicyclonon-4-ene gives trans, trans-2,6-dibromo-9-oxabicyclononane and trans,trans-2,5-dibromo-9-oxabicyclononane.Sequential bromination and Bu3SnH reduction converts 1,2-epoxyhex-5-ene into cis- and trans-2,5-dimethyltetrahydrofuran and 2-methyltetrahydropyran while (+)-cis-limonene oxide is converted into non-chiral cineole.
STEREOSELECTIVE SYNTHESIS OF CYCLIC ETHERS VIA BROMINE ASSISTED EPOXIDE RING EXPANSION
Davies, Stephen G.,Polywka, Mario E. C.,Thomas, Susan E.
, p. 1461 - 1464 (2007/10/02)
9-Oxabicyclonon-4-ene reacts with bromine to give stereoselectively trans,trans-2,6-dibromo-9-oxabicyclononane and trans,trans-2,5-dibromo-9-oxabicyclononane.
ELECTROPHILE AND SOLVENT DEPENDENT SYNTHESES OF CYCLIC ETHERS FROM (Z,Z)-CYCLOOCTA-1,5-DIENE.
Haufe, Guenter
, p. 4365 - 4368 (2007/10/02)
The isomer ratio in the formation of disubstituted 9-oxabicyclo nonane and 9-oxabicyclo nonane derivatives 2 and 3 by an oxyhalogenation procedure depends on the electrophile and on the solvent utilized.
