By Alan R. Katritzky, Otto Meth-Cohn, and Charles W. Rees (Editors-in-Chief)
Quantity three summarises modern tools for the synthesis of useful teams the place carbon is connected to a heteroatom (notably oxygen, nitrogen, and sulphur) by way of a double or triple bond. The synthesis of every kind of carbon and heteroatom substituted, and unsaturated derivatives are introduced jointly in a coherent style, and the place attainable emphasis has been put on selectivity and potency, including sensible functions in genuine events in man made chemistry. hence, the amount covers man made tools for aldehydes and ketones, including their sulphur (ie. thioaldehydes and thioketones), selenium, tellurium, nitrogen (ie. imines, oximes and hydrazones, together with iminium salts and diazo compounds), phosphorus and metal/metalloid analogues. man made equipment for heteroatom substituted aldehydes and ketones and their analogues, eg. carbonyl ylides, also are incorporated, and an intensive account ofketenes and ketenimines and their quite a few heteroatom and steel analogues is given. the quantity additionally covers the original chemistry linked to the synthesis of nitriles and N-substituted nitriles, including isonitriles and all their heteroanalogues.
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Additional info for Comprehensive Organic Functional Group Transformations, Volume 3 (Synthesis:Carbon with One Heteroatom Attached by a Multiple Bond)
Hydroxy aldehydes ð75S663Ł[ R1 R1 R2 OH R2Li, –78 °C O (CO)3Fe (CO)3Fe (23) Scheme 31 O i, H2O2, NaOH ii, O3, MeOH R1 R2 OH 20 Bearin` an Oxy`en 2[90[3[0[1 b! oxoammonium salts ð89JOC351Ł\ and the yields are very high[ In the oxidation of 0\3! and 0\4! diols the intermediate hydroxy aldehydes often undergo further in situ oxidation to the cor! known instability of hydroxy aldehydes due to isomerization\ oxidation or dimer! butyl ether acts as a formyl anion in its reaction with aldehydes\ and the resulting alcohol can be acylated prior to release of the carbonyl ð80SL490Ł\ and methyl!
Phosphate "Equation "37## ð67JOC2677Ł or by condensation of a formyl phosphonate with an amine[ In the latter case\ further methylation or benzylation of the magnesium salt occurs exclusively on carbon "Scheme 51# ð58JCS"C#359Ł[ The parent compound for this class\ formylmethyl phosphonic acid "59#\ is a known compound ð58JOC644Ł[ O P R2O R 2O O BunLi then DMF R1 Li O P R2O R2O H3O+ NMe2 50–90% R1 O P CHO R2O 2 R O R1 Scheme 61 O P PriO i Pr O NMe2 (59) O i, LDA, –78 °C P EtO EtO NBut ii, (EtO)2POCl O P EtO EtO O CHO cyclohexylamine 75% (48) NHBut O P EtO EtO N c-C6H11 ii, MeI 40% H Scheme 62 O P HO HO (60) i, EtMgBr CHO P EtO EtO N H c-C6H11 49 Alkyl Aldehydes The attack of phosphorus"III# nucleophiles at imines or halides has been used to prepare formyl!
NHR! amino aldehydes are potentially applicable to the synthesis of more remote positional isomers[ Thus\ procedures involving oxidation\ reduction using the Rosenmund reaction ð89HCA394Ł or LiAlH3 ð89TL6208Ł\ halide displacement\ nucleophilic addition and oxidative cleavage are all appropriate for the synthesis of a variety of amino aldehydes[ The reductive amination of aldehydes or ketones is often done using conditions where acid! sensitive groups do not survive[ Using Ti"OPri#3 as a Lewis acid catalyst and NaBH2CN as the reducing agent\ cyclic and acyclic acetals remain intact\ demonstrating the usefulness of this pro!
Comprehensive Organic Functional Group Transformations, Volume 3 (Synthesis:Carbon with One Heteroatom Attached by a Multiple Bond) by Alan R. Katritzky, Otto Meth-Cohn, and Charles W. Rees (Editors-in-Chief)