By Scott E. Denmark
Natural Reactions is a set of chapters, each one dedicated to a unmarried response or a definitive part of a response of extensive applicability, with specific realization given to boundaries, interfering affects, results of constitution, and the choice of experimental innovations.
quantity seventy one contains a bankruptcy on Ionic and Organometallic-Catalyzed Organosilane savings.
- Includes tables that comprise all attainable examples of the reactions into account
- Each response is totally referenced to the first literature
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Extra info for Organic Reactions, Vol. 71
This distinction serves as a basis for selectivity of reduction. Under essentially every set of conditions reported, 1-methylcyclohexene, which forms a tertiary aliphatic carbenium ion upon protonation, undergoes reduction to methylcyclohexane in good to excellent yields, whereas cyclohexene, which can only form a secondary aliphatic carbenium ion intermediate upon protonation, does not normally undergo reduction. 231 An exception is reported when the reactions are conducted using a twofold excess of dichloroethylsilane with equal equivalents of either aluminum chloride or aluminum bromide and p-toluenesulfonic acid at 40◦ for two hours in dichloromethane.
196,273 The combinations of Ph2 SiH2 / Pd(P(Tol-p)3 )4 /ZnCl2 274 and Et3 SiH/TFA275 are also employed in this transformation. PMHS, Pd(PPh3)4 + PPh3, THF, 5 d OAc (48%) (52%) (Eq. 130) OAc Ph2SiH2, Pd(PPh3)4 CN THF, rt, 30 h CN (Eq. 131) (100%) The Et3 SiH/TFA reduction of a 3-acetoxy enol ether is reported. The diastereoselectivity is high for the Z isomer, but much lower for the E isomer (Eq. 276 BnO Ph PhMe2SiH, TFA OAc rt, 16 h BnO Ph BnO OAc + Ph OAc (Eq. 277 Use of an excess of the triethylsilane can give 52 ORGANIC REACTIONS further reduction to the methyl group.
19 TFA, rt (Eq. 76) Trisubstituted Alkenes. With very few exceptions, trisubstituted alkenes that are exposed to Brønsted acids and organosilicon hydrides rapidly undergo ionic hydrogenations to give reduced products in high yields. 134,146,192,202,203,207 – 210,214,234 When 1-methylcyclohexene is reduced with one equivalent of deuterated triethylsilane and two equivalents of trifluoroacetic acid at 50◦ , methylcyclohexane1-d1 is obtained in 80% yield after 24 hours (Eq. 221 D Et3SiD (80%) (Eq.