By Alan R. Katritzky, Otto Meth-Cohn, and Charles W. Rees (Editors-in-Chief)
During this quantity, containing 24 chapters dedicated to carbon connected via singlebonds to 2 heteroatoms, the reader will locate numerous chapters reviewing the synthesis of generic useful teams, particularly acetals, dithioacetals, aminals and some of the combined species. The derivatives with tetracoordinated (saturated) carbon are defined partially I and people, eg. ketene acetals, of tricoordinated carbon partly II. even though, the remedy is entire and the authors have exposed a lot interesting chemistry pertaining to much less everyday teams, together with a few like geminal halohydrins, halo amines and diols that areoften risky. back, an incredibly huge variety of compounds having metals hooked up to an identical carbon were situated within the literature, and the abundance of phosphorus derivatives, eg. people with geminal nitrogen features, displays their value as biologically lively species and as intermediates in synthesis. half III contains a unmarried, brief bankruptcy describing dicoordinate carbon (carbenes) and examples of carbon cations,anions and radicals. right here the remedy is intentionally selective because during the paintings as an entire emphasis is put on the synthesis of isolable species instead of the brief intermediates of natural reactions.
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Extra resources for Comprehensive Organic Functional Group Transformations, Volume4 (Synthesis: Carbon with Two Heteroatoms, Each Attached by a Single Bond)
Bromo! dimethylaminopyridine "dmap#\ or potassium ~uoride and 07! butyl carbonate\ which has been used to introduce the t! chloro! chloroethyl chloroformate and allyl! ~uoro sul_de groups[ Product Reagent X Substrate 96 85 91 89 83 91JOC6878 88TL5729 91JOC6878 91JOC6878 91JOC6878 O NH NH F N Y O N O AcO X = OMe X = OMe X = OMe X = OAc X = OAc a Ref. X O S Yield (%) O O OAc AcO DASTa(SbCl3) DAST(SbCl3) XeF2 DAST(SbCl3) XeF2 OAc X = OMe, Y = S(O) X = OMe, Y = S(O) X = OMe, Y = S X = OAc, Y = S(O) X = OAc, Y = S DAST = diethylaminosulfur trifluoride.
Chloro ethers and bromine\ through a process of dehydro! ~uoroalkyl acetate "24# "Equation "15## ð81JA6532Ł[ The ~uoro lactone "25# is also formed by the addition of a reagent containing ~uorine to a vinyl acetate^ in this case the reagent\ benzeneselenenyl ~uoride\ is formed in situ by the reaction of silver ~uoride with benzeneselenenyl chloride "Equation "16## ð89TL862Ł[ An example of the opposite approach is the formation in reportedly good yield of the a! Fluoroalkyl esters have also been prepared by substitution reactions\ which include that of per~uoroacyl ~uorides with the per~uoro alkoxide "30# at −072>C to give the per~uoro esters "31#\ which are said to be stable at 14>C and above when pure ð61JOC2221Ł\ and the reaction of ethyl 0!
Iodoalkyl esters\ R01CIOCOR1 The Finkelstein reaction is the only method which has been employed for the synthesis of a! chloroalkyl carbonochloridates# is a special case of the carbonyl chloroacylation reaction used to synthesise a! chloroalkyl esters and involves the reaction of liquid phosgene with an aldehyde in the presence of a quaternary ammonium salt "Equation "30## ð70EUP39042\ 73JOC1970\ 75S516\ 89JOC1139Ł^ the reaction is applicable to alkyl\ aromatic and heterocyclic aldehydes ð72GEP2130457Ł[ The uncatalysed reaction between chloral and phosgene in dry benzene also gives a reasonable yield of the adduct "42# ð46JCS507Ł[ Trichloromethyl carbonate can be used as an in situ source of phosgene and thus 48 Halo`en and Oxy`en constitutes an attractive alternative to the liquid form of this reagent "Equation "31## ð78TL1922Ł[ Although the photochemical chlorination of methyl chloroformate gives chloromethyl chloro!
Comprehensive Organic Functional Group Transformations, Volume4 (Synthesis: Carbon with Two Heteroatoms, Each Attached by a Single Bond) by Alan R. Katritzky, Otto Meth-Cohn, and Charles W. Rees (Editors-in-Chief)