77196-22-6Relevant academic research and scientific papers
Synthesis of 1,5-Dienes via Photocycloaddition between 2,5-Dihydrothiophene 1,1-Dioxides (Sulfolenes) and α,β-Unsaturated Cyclic Ketones and Anhydrides. Synthesis of 10-Hydroxygeraniol
Williams, John R.,Lin, Charles,Chodosh, Daniel F.
, p. 5815 - 5822 (1985)
Photocycloaddition between 2,5-dihydrothiophene 1,1-dioxide (1a) and 2-cyclohexenones 2a,b afforded cis-anti-cis and cis-trans photoadducts 3a,b and 4a in low yield.Photocycloaddition between sulfolene 1a and 2-cyclopentenones 8a,b yielded cis-anti-cis ph
Flash Vacuum Pyrolysis of the 3-Thiabicycloheptane 3,3-Dioxide Ring System: a New Stereospecific Synthesis of cis-1,2-Divinyl Derivatives
Cadogan, J. I. G.,Gosney, Ian,McLaughlin, Leo M.,Hamill, Brendan J.
, p. 1242 - 1243 (1980)
A short and stereospecific route to cis-1,2-divinyl compounds from derivatives of the readily available 3,3-dioxide (1) of 3-thiabicycloheptane-6,7-dicarboxylic anhydride by cheleotropic elimination of SO2 is reported.
Pyrolysis of tricyclic cyclobutane-fused sulfolanes as a route to cis-1,2-divinyl compounds and their Cope-derived products
Aitken, R. Alan,Cadogan, J. I. G.,Gosney, Ian,Humphries, Caroline M.,McLaughlin, Leo M.,Wyse, Stuart J.
, p. 605 - 614 (2007/10/03)
Functionalisation of the double bond of 3-thiabicyclohept-6-ene 3, readily formed by hydrolysis of the cycloadduct 1 of 3-sulfolene and maleic anhydride followed by oxidative bis-decarboxylation, gives tricyclic sulfones 5-7 and 9 with the bicyclo2,4> skeleton. FVP of 3 results in stereospecific extrusion of SO2 to give Z-hexa-1,3,5-triene which undergoes electrocylisation to give cyclohexa-1,3-diene while reaction of 3 with LiAlH4 results in non-stereospecific extrusion to give Z- and E-hexa-1,3,5-triene. Upon FVP the tricyclic sulfones 5-7 and 9 lose SO2 to give 7-membered ring products 16-19 by Cope rearrangement of the initially formed cis-1,2-divinyl intermediates 15. The 1,3-dipolar cycloaddition of nitrile oxides and a nitrone to the double bond of 3 gives tricyclic sulfones with the tricyclo2,6> skeleton and a wider variety of these can be prepared by conventional reactions of 1. Upon FVP these lose SO2 to give stable cis-1,2-divinyl compounds 23, 24, 37-40 and 41-44. The Diels-Alder adducts 48 and 49 have been prepared from 3 and these behave differently upon FVP, losing SO2 and butadiene to give tetrasubstituted benzenes, in the latter case by way of an unexpected tetracyclic intermediate.
A Simple, Stereocontrolled Synthesis of E,Z-1,5-Dienes
Cadogan, J. I. G.,Buchan, Caroline M.,Gosney, Ian,Hamill, Brendan J.,McLaughlin, Leo M.
, p. 325 - 326 (2007/10/02)
The readily available 3,3-dioxide (1) of 3-thiabicycloheptane-6,7-dicarboxylic anhydride acts as a general synthetic precursor for E,Z-1,5-dienes such as (4a-e) via functionalisation followed by thermal extrusion of SO2.
