139928-65-7Relevant academic research and scientific papers
Copper-catalysed meso-bislactone ring opening using Grignard and mixed triorganozinc reagents
Borthwick, Scott,Dohle, Wolfgang,Hirst, Paul R.,Booker-Milburn, Kevin I.
, p. 7205 - 7208 (2006)
An efficient copper-mediated SN2′ ring-opening reaction of a meso-bislactone has been developed using Grignard reagents and, for the first time, mixed triorganozinc reagents.
Palladium-Catalyzed [2+1] Cycloadditions Affording Vinylidenecyclopropanes as Precursors of 7-Membered Carbocycles
Lepronier, Aymeric,Achard, Thierry,Giordano, Laurent,Tenaglia, Alphonse,Buono, Gerard,Clavier, Herve
, p. 631 - 642 (2016/02/27)
Palladium(II) acetate in association with secondary phosphine oxides provides an efficient catalytic system for [2+1] cycloadditions starting from oxanorbornene derivatives and tertiary propargyl esters giving rise to vinylidenecyclopropanes. This reaction is specific to bidentate phosphinito-phosphinous acid ligands generated from secondary phosphine oxides. The [2+1] cycloaddition was found broad in scope with a high tolerance to various functional groups. Moreover, vinylidenecyclopropanes were straightforwardly converted into oxabicyclo[3.2.1]oct-2-ene derivatives through a palladium-catalyzed ring-expansion. Finally, the oxa bridge cleavage of oxatricyclic compounds yields functionalized 7-membered carbocycles.
An Investigation of the Retro Diels-Alder Reaction as a Method for the Generation of Diatomic Sulfur
Gilchrist, Thomas L.,Wood, Jane E.
, p. 9 - 16 (2007/10/02)
The cyclic disulfides 2,3-dithiabicyclooct-5-ene 5, 1,4-dihydro-2,3-benzodithin 6 and hexahydro-5,8-epoxy-2,3-benzodithiin 7 have been prepared by oxidation of the corresponding dithiols.Each of these compounds has been subjected to vapour phase pyrolysis in order to determine whether a retro Diels-Alder reaction occurs, leading to the formation of diatomic sulfur (S2) and a diene.Compounds 5 and 7 both appeared to decompose in this way; in each case the expected diene was detected in the pyrolysate together with sulfur (S8).Attempts to intercept S2 and thus to obtain direct evidence for its formation were not successful.The benzodithiin 6 underwent an analogous loss of sulfur on vapour phase pyrolysis, but only as a minor reaction pathway, and this decomposition pathway was not detectable in solution pyrolyses.Solution pyrolysis of 6 in the presence of N-phenylmaleinimide gave N-phenyl-2,3-naphthalimide 21 in low yield. cis-Cyclopentene-3,5-dithiol 9 has also been prepared but no evidence could be obtained for the formation of disulfide 4 on oxidation.Reaction of the dithiol 9 with aldehydes and ketones in the presence of acids led to the formation of adducts (such as 12 and 13 from acetone) which were rapidly interconverted in acidic media.
