75480-69-2Relevant academic research and scientific papers
Indium-mediated mild and efficient one-pot synthesis of alkyl phenyl selenides
Munbunjong, Wanida,Lee, Eun Hwa,Chavasiri, Warinthorn,Jang, Doo Ok
, p. 8769 - 8771 (2005)
A mild and convenient one-pot process for synthesizing alkyl phenyl selenides is developed using indium metal. The reaction shows the selectivity for tert-alkyl, benzylic, and allylic halides over primary and secondary alkyl halides.
Preparation of adamantyl sulfides with [bis(1-adamantanecarboxy)iodo]arenes and disulfides
Togo,Muraki,Yokoyama
, p. 155 - 157 (1995)
Irradiation of [bis(1-adamantanecarboxy)iodo]arenes with a high-pressure mercury lamp in the presence of disulfides gives the corresponding adamantyl sulfides in high yields. This reaction proceeds via the radical decarboxylation of [bis(1-adamantanecarbo
Syntheses of sulfides and selenides through direct oxidative functionalization of C(sp3)-H bond
Du, Bingnan,Jin, Bo,Sun, Peipei
supporting information, p. 3032 - 3035 (2014/06/23)
A new protocol for C-S and C-Se bond formation by the direct functionalization of the C(sp3)-H bond of alkanes under metal-free conditions was developed. Using tBuOOtBu as the oxidant, the reaction of disulfides or diselenides with alkanes gave sulfides or selenides in moderate to good yields. The method was very simple and atom-economical.
Indium-mediated cleavage of diphenyl diselenide and diphenyl disulfide: efficient one-pot synthesis of unsymmetrical diorganyl selenides, sulfides, and selenoesters
Munbunjong, Wanida,Lee, Eun Hwa,Ngernmaneerat, Poonlarp,Kim, Sung Jun,Singh, Gurpinder,Chavasiri, Warinthorn,Jang, Doo Ok
experimental part, p. 2467 - 2471 (2009/08/15)
A convenient and efficient method was developed for the synthesis of alkyl phenyl selenides, sulfides, and selenoesters in one-pot reaction by using indium metal. The reaction showed the selectivity for tert-alkyl, benzylic, and allylic halides over primary and secondary alkyl halides. For the reaction of primary and secondary alkyl iodides and bromides, the yields of selenides were improved by the addition of a catalytic amount of iodine.
Zinc-mediated synthesis of tertiary alkyl selenides from tertiary alkyl halides
Krief, Alain,Derock, Michel,Lacroix, Damien
, p. 2832 - 2834 (2007/10/03)
Diorganyl selenides are efficiently synthesized from tertiary alkyl halides, selenols or selenolates and zinc dibromide as well as from diselenides in the presence of zinc. Georg Thieme Verlag Stuttgart.
General synthesis of alkyl phenyl selenides from organic halides mediated by zinc in aqueous medium
Bieber, Lothar W.,De Sá, Ana C.P.F.,Menezes, Paulo H.,Gon?alves, Simone M.C.
, p. 4597 - 4599 (2007/10/03)
Organic halides of different structural types react with diphenyl diselenide and zinc dust in aqueous medium to give alkyl phenyl selenides. Benzylic and allylic bromides, α-bromoesters, acids and ketones and some primary alkyl iodides produce high yields even under acidic conditions. Less reactive halides need basic medium. The reaction proceeds equally well in the presence of various unprotected functional groups. Control experiments support a SH2 mechanism via alkyl radicals.
Redox-Mediated Decarboxylative Photo-Phenylselenenylation of N-Acyloxyphthalimides
Okada, Keiji,Okubo, Katsura,Morita, Naoto,Oda, Masaji
, p. 2021 - 2024 (2007/10/02)
Decarboxylative phenylselenenylation of N-acyloxyphthalimides by visible light irradiation in aqueous solvents using catalytic amount of Ru(bpy)3Cl2 as a sensitizer in the presence of one equivalent of BNAH and 0.5 equivalent of diphenyl diselenide effici
The invention of radical reactions. Part XXXI. Diphenylsilane: A reagent for deoxygenation of alcohols via their thiocarbonyl derivatives, deamination via isonitriles, and dehalogenation of bromo- and iodo- compounds by radical chain chemistry
Barton, Derek H. R.,Jang, Doo Ok,Jaszberenyi, Joseph Cs.
, p. 7193 - 7214 (2007/10/02)
Various thionocarbonates and xanthates of alcohols and bis-xanthates of vic-diols are readily deoxygenated to the corresponding hydrocarbons or olefins, while bromides and iodides are dehalogenated with diphenylphenylsilane in good yield.
Photochemistry of phenyl thioethers and phenyl selenoethers. Radical vs ionic behavior
Kropp, Paul J.,Fryxell, Glen E.,Tubergen, Mark W.,Hager, Michael W.,Harris Jr., G. Davis,McDermott Jr., T. Paul,Tornero-Velez, Rogelio
, p. 7300 - 7310 (2007/10/02)
In analogy with alkyl iodides and bromides, the phenyt thio- and selenoethers 2a,b, 13a, 21b,c and 35 displayed competing radical and ionic photobehavior on irradiation in solution, via a mechanism thought to involve initial homolytic cleavage of the alkyl C-S or C-Se bond followed by electron transfer within the resulting radical pair cage (Scheme I). These are the first examples of ionic photobehavior to be recognized for the C-SAr and C-SeAr chromophores. The electronegatively substituted pentafiuorophenyl analogues 2c, 13b, and 21d displayed enhanced ionic photobehavior. By contrast, the 4-methoxyphenyl derivative 21a exhibited almost exclusively radical behavior. The sulfoxide (2R*,R*s)-21f displayed principally radical behavior, accompanied by epimerization at sulfur. The quantum yields for the disappearance of the 2-norbornyl ethers 21b and 21c were 0.53-0.64 in solution and rose to 0.89-0.95 in the presence of suspended fumed silica. Irradiation of the phenyl thioether 21b on silica gel resulted in nucleophilic trapping by surface silanol groups to afford covalently bound material (33), which afforded chloride 34 on treatment with SOCl2. Irradiation of phenyl thioethers 2a and 35, phenyl selenoether 2b, or C6H5SH in allyl alcohol solution afforded acetal 11, apparently via isomerization of some of the solvent to propanal (44) followed by acetalization. Irradiation of alcoholic solutions of aldehydes containing C6H5SH is a useful means of generating acetals under neutral conditions.
