EurekaMag.com logo
+ Site Statistics
References:
53,869,633
Abstracts:
29,686,251
+ Search Articles
+ Subscribe to Site Feeds
EurekaMag Most Shared ContentMost Shared
EurekaMag PDF Full Text ContentPDF Full Text
+ PDF Full Text
Request PDF Full TextRequest PDF Full Text
+ Follow Us
Follow on FacebookFollow on Facebook
Follow on TwitterFollow on Twitter
Follow on LinkedInFollow on LinkedIn

+ Translate

Iron(II)-promoted rearrangement of 1,4-diaryl-2,3-dioxabicyclo(2.2.2)oct-5-enes: A mechanism distinct from that postulated previously



Iron(II)-promoted rearrangement of 1,4-diaryl-2,3-dioxabicyclo(2.2.2)oct-5-enes: A mechanism distinct from that postulated previously



Tetrahedron Letters 43(46): 8313-8317



Reactions of 1,4-diaryl-2,3-dioxabicyclo(2.2.2)oct-5-enes 1a-c (1a: Ar=p-FC6H4, 1b: Ar=C6H5, 1c: Ar=p-MeC6H4) with FeBr2 afforded syn-1,2;3,4-bis(epoxy)-1,4-diarylcyclohexanes 4a-c and cis-3,6-diaryl-2,3-epoxycyclohexanones 5a-c as major products instead of the previously reported 1-aroyl-3-aryl-2,3-epoxycyclopentanes 2a-c.

(PDF emailed within 1 workday: $29.90)

Accession: 010885456

Download citation: RISBibTeXText



Related references

Iron -promoted rearrangement of 1,4-diaryl-2,3-dioxabicyclo oct-5-enes A mechanism distinct from that postulated previously. Tetrahedron Letters 43(46): 8313-8317, 11 November, 2002

Unexpected selectivity between pinacolic rearrangement and intramolecular displacement in the acid-promoted epoxide ring opening of 6-exo-cyano-3,8-dioxabicyclo oct-6-endo-yl esters. Tetrahedron 50(8): 2469-2478, 1994

Intramolecular hydrogen abstraction reaction promoted by alkoxy radicals in carbohydrates. Synthesis of chiral 2,7-dioxabicyclo[2.2.1]heptane and 6,8-dioxabicyclo[3.2.1]octane ring systems. Journal of Organic Chemistry 67(21): 7439-7445, 2002

Intramolecular hydrogen abstraction reaction promoted by alkoxy radicals in carbohydrates. Synthesis of chiral 2,7-dioxabicyclo(2.2.1)heptane and 6,8-dioxabicyclo(3.2.1)octane ring systems. Journal of Organic Chemistry 67(21): 7439-7445, 2002

Intramolecular hydrogen abstraction reaction promoted by alkoxy radicals in carbohydrates Synthesis of chiral 2,7-dioxabicyclo heptane and 6,8-dioxabicyclo octane ring systems. Journal of Organic Chemistry 67(21): 7439-7445, October 18, 2002

Trisubstituted oxetanes from 2 7 dioxabicyclo 3 2 0 hept 3 enes. Tetrahedron Letters 31(33): 4693-4696, 1990

Mechanism of thermal rearrangement of the spiro bicyclo[2.1.0]-pentane-5,2'-methylenecyclopropanes to 6- and 7- methylenebicyclo[3.2.0]hept-1-enes. Proceedings of the National Academy of Sciences of the United States of America 77(6): 3090-3094, 1980

Palladium-catalyzed oxidative rearrangement of diaryl alkenyl carbinols to β,β-diaryl α,β-unsaturated ketones. Organic Letters 13(14): 3648-3651, 2011

Wagner-Meerwein skeletal rearrangement of 3-spiroannulated 6,8a-epoxy- and 6,8a;7,8-diepoxyisoquinolines (3-aza-11-oxatricyclo[6.2.1.0(1,6)]undec-9-enes). Isolation and identification of 5-aza-2-oxatricyclo[6.2.1.0(3,9)]undec-3-enes. Journal of Organic Chemistry 69(2): 432-438, 2004

A general strategy for the diastereoselective synthesis of 2,6-diaryl-3,7-dioxabicyclo[3.3.0]octane lignans. Journal of Organic Chemistry 68(23): 9159-9161, 2003

Analysis of 2 6 diaryl 3 7 dioxabicyclo 3.3.0 octanes and dibenzylbutyrolactones by pyrolysis gas chromatography mass spectrometry. Journal of Analytical and Applied Pyrolysis 23(2): 135-152, 1992

A general synthesis of 2 6 diaryl 3 7 dioxabicyclo 3.3.0 octane lignans applicable to unsymmetrically substituted compounds. Journal of the Chemical Society Perkin Transactions I (3): 587-594, 1985

Iron promoted conjugate addition: implication of the six-centered mechanism based on the isolation of the iron-enolate intermediate. Chemical Communications 48(100): 12231-3, 2012

Synthesis and cytotoxicity of a novel 1-alkylaminomethyl-2,4-diaryl-butadiene-1,3 fragment integrated within cyclohex(pent)enes. Farmaco 59(5): 373-379, 2004

Synthesis, Fe -induced degradation, and antimalarial activities of 1,5-diaryl-6,7-dioxabicyclo nonanes Direct evidence for nucleophilic O-1,2-aryl shifts. Tetrahedron Letters 43(11): 2063-2067, 11 March, 2002