873988-63-7

Upstream product

• 95102-89-9 Ethyl 2-methyl-3-phenyl-2-butenoate 
• 91968-14-8 2-Methyl-3-phenyl-butane-1,3-diol 
• 64-17-5 ethanol 
• 109640-15-5 ethyl 2-methyl-3-phenylbutanoate 
• 219547-24-7 [(3-iodo-2-methylbutan-1-oxy)diphenylsilyl]trimethylsilane 
• 216592-89-1 3-iodo-2-methylbutyl benzenesulfonate 

Downstream Products

• 97416-75-6 2-methyl-3-phenylbutanal 
• 129254-78-0 (3-bromo-1,2-dimethyl-propyl)-benzene 

Relevant academic research and scientific papers

Stereoselective radical Aryl migration reactions from sulfur to carbon

Stereoselective aryl migration reactions from sulfur in sulfonates and sulfonamides to C-centered radicals are reported. The 1,5-aryl migration from sulfur to differently substituted C-centered radicals could be performed with high yields and selectivities. Functionalized aryl groups could also be transferred by this new method. A model to explain the stereochemical outcome of the reaction is presented and some mechanistic aspects of this reaction are discussed. Aryl migration reactions from sulfur in sulfinates to carbon radicals were less efficient, and the corresponding migrations in aryl sulfoxides were not observed at all. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

Stereoselective radical aryl migration from silicon to carbon

Highly diastereoselective radical 1,5 phenyl migration reactions from silicon in diarylsilyl ethers to various C-centered radicals to form the corresponding 3-phenylated alcohols are described. Functionalized aryl groups can also be transferred. The effect of the variation of the attacking radical on the aryl transfer reaction is discussed. Best results are obtained for the phenyl migration to nucleophilic secondary alkyl radicals, where high yields (up to 81%) and high selectivities (up to 95% ds) have been obtained. The mechanism of the process is discussed and a model to explain the stereochemical outcome of the reaction is presented. Finally, stereoselective 1,4 aryl migration reactions from Si to C, including a new method for the α- arylation of esters, are presented.

SELECTIVE REDUCTION OF DIARYL OR ARYL ALKYL ALCOHOLS IN THE PRESENCE OF PRIMARY HYDROXYL OR ESTER GROUPS BY ETHERATED BORON TRIFLUORIDE-TRIETHYLSILANE SYSTEM

Diaryl or alkyl aryl carbinols bearing a second reducible functional group (such as hydroxyl or ester) are selectively deoxygenated in high yields by the action of etherated boron trifluoride and triethyl silane reducing system.