65108-53-4Relevant academic research and scientific papers
Contrasting reactivity in Lewis acid-promoted reactions of thio- and silyl-allenes with 1,4-benzoquinones
Engler, Thomas A.,Agrios, Konstantinos,Reddy, Jayachandra P.,Iyengar, Rajesh
, p. 327 - 330 (1996)
In Ti(IV)-promoted reactions with 2-methoxy-1,4-benzoquinones 3, thioallenes 1 give 2 + 2 and/or 3 + 2 products via attack on a C = C moiety of the quinone, whereas silylallene 2 gives products derived from attack on a carbonyl group of the quinone.
Controlled Carbon-Sulphur or Carbon-Silicon Bond Cleavage in the Reactions of Alkyl-lithium Reagents with a 1-Silyl-1-thioallene
Bridges, Alexander J.,Fedij, Victor,Turowski, Eugene C.
, p. 1093 - 1095 (1983)
3-Methyl-1-phenylthio-1-trimethylsilylbuta-1,2-diene (3) reacts with different alkyl-lithium reagents by C-Si or C-S bond cleavage, rather than by Michael addition or metallation; one product, the α-silyl-α-lithioallene (6), is alkylated mainly γ with carbonyl compounds, but is silylated α with Et3SiCl to form the 1,1-bis-silylallene Me2C=C=C(SiEt3)SiMe3.
Studies on the regio- and stereoselectivity of halohydroxylation of 1,2-allenyl sulfides or selenides
Ma, Shengming,Hao, Xueshi,Meng, Xiaofeng,Huang, Xian
, p. 5720 - 5724 (2007/10/03)
It was observed that the halohydroxylation of 1,2-allenyl sulfides or selenides with Br2 (CuBr2 or NBS) or I2 and water demonstrated a fairly good regioselectivity (i.e., the C=C bond that is remote from the S or Se atom w
o-quinone methides from 4-allenylcyclobutenones: Synthesis and chemistry
Taing, Meng,Moore, Harold W.
, p. 329 - 340 (2007/10/03)
Selected 4-allenylcyclobutenones ring expand to the corresponding o-quinone methides upon thermolysis in refluxing toluene or benzene. These reactive intermediates were not isolated but trapped to give stable products. The reaction has synthetic potential as a route to highly-substituted phenols, benzofurans, and aryl analogs of hexahydrocannabinol. In addition, a unique rearrangement involving a methyl migration from silicon to carbon of selected 4-[3,3-bis(trimethylsilyl)-1,2-propadienyl]cyclobutenones to give 1,2-benzoxasilols is described. Finally, data are presented that show rapid rotation around the alkylidene bond of o-quinone methides at 30°C and that 2-(1-methylethenyl)phenols are in equilibrium with the corresponding o-quinone methides.
Chemistry of Allene Sulphoxides: Novel Transformations of Acetylenic Alcohols
Cutting, Ian,Parsons, Philip J.
, p. 1209 - 1210 (2007/10/02)
The preparation and reactions of allenes derived from 1-phenylthio substituted acetylenic alcohols are described; this chemistry offers new routes to allenyl sulphides, acyl anion equivalents, and substituted unsaturated aldehydes.
Thermal and Photochemical Reactions of Organocobaloximes with Diphenyl Disulphide and Diphenyl Diselenide
Deniau, Jean,Duong, Kiem N. V.,Gaudemer, Alain,Bougeard, Peter,Johnson, Michael D.
, p. 393 - 398 (2007/10/02)
Alkyl- and benzyl-bis(dimethylglyoximato)pyridinecobalt(III) complexes react with diphenyl disulphide or diphenyl diselenide, thermally and photochemically, to give good yields of alkyl or benzyl phenyl sulphides or selenides.Chiral alkylcobalt(III) complexes react to give racemic alkyl phenyl sulphides or selenides.Allyl- and propadienyl-bis(dimethylglyoxymato)pyridinecobalt(III) complexes react similarly to give the thermodynamically more stable allyl, propadienyl, or propynyl phenyl sulphides or selenides.These reactions are interpreted in terms of free radical processes in which organic radicals formed as a result of thermal, photochemical, or chemically induced homolysis of the organocobalt complex, attack the diphenyl dichalcogenide to give the product organo phenyl chalcogenide.No evidence could be obtained for the direct attack of phenylthiyl or phenylselenyl radicals on the organic ligand of the organocobalt complexes, though this process cannot be excluded in the case of allylcobalt complexes.
PHENYLTHIOCOPPER TRIMETHYLPHOSPHITE COMPLEX. A REAGENT FOR THE PREPARATION OF THIOALLENES.
Bridges, Alexander J.
, p. 4401 - 4404 (2007/10/02)
The title complex reacts with propargyl halides and, in situ generated, propargyl mesylates to produce thioallenes in good yields, via an allylic inversion.
