Organic Reactions, Vol. 71 by Scott E. Denmark

By Scott E. Denmark

Natural Reactions is a suite of chapters, each one dedicated to a unmarried response or a definitive section of a response of broad applicability, with specific recognition given to boundaries, interfering affects, results of constitution, and the choice of experimental innovations.

quantity seventy one incorporates a bankruptcy on Ionic and Organometallic-Catalyzed Organosilane rate reductions.

  • Includes tables that comprise all attainable examples of the reactions into consideration
  • Each response is totally referenced to the first literature

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236 Many of these reductions are highly stereoselective. For example, treatment of ORGANOSILICON HYDRIDE REDUCTIONS 39 2-phenylnorbornene with a solution of trifluoroacetic acid and triethylsilane in dichloromethane is reported to yield only endo-2-phenylnorbornane (Eq. 164 Et3SiH Ph (Eq. 78) (100%) TFA, CH2Cl2 Ph A mixture of Et3 SiH/TFA in dichloromethane reduces 3-methyl-5-α-cholest2-ene to give the pure equatorial methyl isomeric product, 3β-methyl-5αcholestane, in 66% yield (Eq. 126 On the other hand, attempts to reduce cholest-5-ene using the same technique yield neither 5α-cholestane nor 5βcholestane, but instead an isomeric mixture of rearranged olefins.

89) No Reaction TFA (Eq. 88) Additional evidence of this pattern of behavior is shown upon treatment of the conjugated diene 1-propenylcyclohexene with two equivalents of triethylsilane and three equivalents of trifluoroacetic acid at 50◦ . This diene gives a 70% yield of completely reduced propylcyclohexane after 10 hours (Eq. 231 No partially reduced intermediates are found. Et3SiH (70%) TFA (Eq. 90) Similar treatment of the isomeric, nonconjugated 1-(3-propenyl)cyclohexene gives a mixture of products containing 55% of the partially reduced 3-propenylcyclohexane and 15% of the completely reduced propylcyclohexane (Eq.

Further ORGANOSILICON HYDRIDE REDUCTIONS 37 exposure of the reaction mixture to the reaction conditions does not result in additional hydrocarbon formation from the ester. Et3SiH + O2CCF3 TFA (Eq. 1] heptane (Eq. 71). The same product is formed in 37% yield after only five minutes. 1]heptyl trifluoroacetates that remains inert to the reaction conditions. 1]heptane product with an exo-deuterium at the tertiary carbon position shared with the methyl group. 230 Et3SiH H(D) + TFA, rt, 24 h (45%) (Eq.

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