73622-43-2Relevant academic research and scientific papers
Studies of the synthesis of 8a-hydroxy-4a-methyloctahydronaphthalen-1(2H)-ones and their 2α-deutero derivatives
Stiver, Shirley,Clark, Peter D.,Yates, Peter
, p. 27 - 34 (2007/10/02)
Two syntheses of the bicyclic α-ketols, 8a-hydroxy-4a-methyl-trans- and -cis-octahydronaphthalen-1(2H)-ones (1 and 2), have been effected.One involves epoxidation of 4a-methyl-1,2,3,4,4a,5,6,7-octahydronaphthalene (4), followed by hydrolysis and oxidation; direct "hydroxy ketonization" of 4 was found not to be practicable.The second involves treatment of 3,4,5,6,7,8-hexahydronaphthalen-1(2H)-one (14) with lithium dimethylcuprate, trimethylsilylation of the resulting enolate, oxidation of the enol ether, and hydrolysis.Syntheses of the 2α-deutero derivatives of 1 and 2 are also described.
THE ALLYLIC ALCOHOL FUNCTION IN ALKYLTIN(IV)-MEDIATED CARBOCYCLIZATION. REGIOSPECIFIC OCTALIN AND HYDRINDENE SYNTHESIS.
Macdonald, Timothy L.,Mahalingam, Sankaran
, p. 2077 - 2080 (2007/10/02)
The employment of the allylic alcohol function in the initiation of tetraalkylstannane-mediated carbocyclization and the application of this methodology to the regiospecific synthesis of Δ1,2-octalins and Δ4,5-hydrindene ring systems
Tri-n-butyltin Hydride: A Selective Reducing Agent for 1,3-Dithiolanes
Gutierrez, Carlos G.,Stringham, Rex A.,Nitasaka, Tadashi,Glasscock, Karl G.
, p. 3393 - 3395 (2007/10/02)
Tri-n-butyltin hydride has been found to be an effective and selective agent for complete or partial desulfurization of 1,3 dithiolanes 1.The reaction of 1 with 4 equiv of tri-n-butyltin hydride in the presence of 2,2'-azobis(isobutyronitrile) results in complete desulfurization, giving hydrocarbons 2 in good yield, ethane and bis(tri-n-butyltin) sulfide.Two equivalents of hydride specifically cleave the two geminal C-S bonds in 1 to give hydrocarbons 2 and bis(tri-n-butylstannyl) ethanedithiolate.One equivalent of tri-n-butyltin hydride reduces 1 quantitatively to the β-ethyl tri-n-butyltin sulfides 11.
