By Alan R. Katritzky, Otto Meth-Cohn, and Charles W. Rees (Editors-in-Chief)
This quantity covers the formation of carbon-carbon single-, double- and triple bonds by means of substitution and addition reactions in addition to through a variety of rearrangements. The formation of carbon-carbon a number of bonds by means of removal and condensation strategies is totally documented. additionally the synthesis of carbon-hydrogen bonds mostly by means of substitution and addition reactions is featured as is the instruction of a wide selection of carbon-centred anions, cations and radicals.
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Extra info for Comprehensive Organic Functional Group Transformations,Volume 1 (Synthesis: Carbon with No Attached Heteroatoms)
5! o} experiment would be prohibitive\ and second the catalyst requires a high percentage of platinum\ thus making the method costly[ Another ~ow method was used to reduce cyano! Ethyladamatane 83 Benzonitrile Methylcyclohexane 64 ÐÐÐÐÐÐÐÐÐÐÐÐÐÐÐÐÐÐÐÐÐÐÐÐÐÐÐÐÐÐÐÐÐÐÐÐÐÐÐÐÐÐÐÐÐÐÐÐÐÐÐÐÐÐÐÐÐÐÐÐÐÐÐÐÐÐÐÐÐ * 30% Ni–Al2O3 CN (35) 180 °C, H2 99% 0[91[0[2[2 Reduction using hydride reagents The use of hydrides for the reduction of nitriles to the methyl analogue seems to have been scarcely investigated to any degree[ Sodium borohydride in acetonitrile was used to reduce p!
90Ł[ The following sections are categorized with respect to the type of nitrogen moiety lost in the deamination[ 0[91[0[0[0 Loss of sulfonamide anion The mechanism for such a reduction is essentially a nucleophilic displacement of a good leaving group by a nucleophilic hydride "Equation "0##[ Sodium borohydride in polar aprotic solvents "hexamethylphosphoramide "HMPA#\ DMSO# furnishes a convenient and e}ective source of nucle! ophilic hydride which may be used for the reductive displacement of disulfonimides[ The incor!
Tives as well as a number of cyclic amines "Scheme 0#[ 18 CarbonÐNitro`en Bonds BH4– R1N(SO2R2)2 R1 H + –N(SO R2) 2 2 (1) HMPA N(Tos)2 NaBH4 HMPA 78% MeO MeO N(Tos)2 MeO MeO 32% Cl Cl N(Tos)2 Cl Cl 22% N(Tos)2 Et 77% ( )9 ( )9 ( )9 N(Tos)2 N(Bros)2 N(Tf)2 N(Bros)2 ( ) 91% ( )8 73% ( )8 36% ( )8 ( ) 66% 6 6 Bros = p-bromobenzene sulfonyl Scheme 1 0[91[0[0[1 Loss of succinimide The development of a monomethylation procedure for aromatic amines ð62JOC0237Ł seren! dipitously led to a method where certain succinimides derived from Mannich bases may be reductively deaminated using sodium borohydride "Equation "1##[ Fortunately\ functionalities such as ester\ nitrile\ or amide do not interfere with the reaction[ There is circumstantial evidence to suggest that the reaction proceeds via a stabilized nitrogen anion\ similar to the case of the sul!
Comprehensive Organic Functional Group Transformations,Volume 1 (Synthesis: Carbon with No Attached Heteroatoms) by Alan R. Katritzky, Otto Meth-Cohn, and Charles W. Rees (Editors-in-Chief)