29329-01-9Relevant academic research and scientific papers
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.
Extension of the Criegee Rearrangement: Synthesis of Enol Ethers from Secondary Allylic Hydroperoxides
Goodman, Richard M.,Kishi, Yoshito
, p. 5125 - 5127 (2007/10/02)
The Criegee rearrangement has been extended to secondary allylic hydroperoxides, allowing for the selective synthesis of cyclic and acyclic enol ethers; the effect of base and electrophilic agent was studied.
An examination of the affect of the epoxide stereochemistry in the nitrogen extrusion from exo- And endo-6,7-diazo-3-oxotricyclo[3.2.2.02,4]Non-6-ene
Liao, Yusheng,White, James B.
, p. 5129 - 5132 (2007/10/02)
The exo and endo isomers of 6,7-diazo-3-oxotricyclo[3.2.2.02,4]non-6-ene have been prepared and their extrusion of nitrogen examined. The exo isomer 10 underwent the expected homo-retro-Diels-Alder reaction at room temperature to give 4,5-dihydrooxepin (11), but the endo isomer extruded nitrogen at>180 °C to give cyclohexenone.
3-Thiabicyclohept-6-ene 3,3-Dioxide: A Novel Synthon for cis-1,2-Divinyl Intermediates and Derived Seven-membered Ring Systems
Aitken, R. Alan,Cadogan, J. I. G.,Gosney, Ian,Hamill, Brendan J.,McLaughlin, Leo M.
, p. 1164 - 1165 (2007/10/02)
Functionalisation of the 6,7-double bond in the novel bicyclic sulphone, 3-thiabicyclohept-6-ene 3,3-dioxide, followed by thermal extrusion of SO2, allows direct entry into seven-membered ring systems via a Cope rearrangement of the resulting cis-1
