By Alan R. Katritzky, Otto Meth-Cohn, and Charles W. Rees (Editors-in-Chief)
An enormous diversity of alternative useful teams is very likely to be had from the attachment of 3 or 4 heteroatoms to carbon. a few of these are abundantly represented within the literature, others are infrequent, and plenty of haven't begun to be defined. the purpose of this quantity is to explain the synthesis of examples of identified practical teams and to spotlight those who are little recognized or unknown. All attainable combos of heteroatoms were surveyed, apart from complexes during which carbon atoms are bonded in basic terms to transition parts. the cloth is organised in 4 elements: tetracoordinated carbon atoms bearing 3 hooked up heteroatoms are lined partially 1, and people bearing 4 heteroatoms partially II; the synthesis of tricoordinated carbonatoms with 3 connected heteroatoms is defined partly III; stabilized radicals and carbocations with 3 hooked up heteroatoms are coated in short partly IV.
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Extra info for Comprehensive Organic Functional Group Transformations, Volume 6 (Synthesis: Carbon with Three or Four Attached Heteroatoms)
Tri~uoromethyl#aziridine "63)# ð55JOC678Ł[ Cyclo! methyl! type processes\ but only moderate yields of addition products are obtained even for addition to such activated systems as acrylonitrile and ethyl acrylate ð68IZV0800Ł[ Dibromo! ), 10 °C, 40 min F 57% NO2 Et (14) Br 5[91[1[0[1 Tetracoordinate carbon atoms bearing one halogen and two nitrogen functions In all cases in which the nitrogen functions are amino groups\ attempts to prepare compounds of this class results in the formation of the corresponding haloiminium salts[ Examples are widespread\ covering simple amines ð54CB0967\ 62LA39\ 64LA084Ł\ cyclic amines ð50CB1483\ 58RTC178Ł and hydra!
Ray radiation to give the corresponding addition products "Scheme 12#[ As expected\ addition of thiolates proceeds without photolytic conditions\ but the reaction rates are heavily dependent on the nature of the haloalkene substitutents[ Mixed chloro! and bromo~uoroalkenes are far more reactive than tetra~uoroethylene\ which requires forcing conditions ð59JA4005\ 50JA739\ 54JOC3900\ 55BCJ1080\ 61JCS"P0#23\ 63JFC"3#096\ 65JCS"P0#0067Ł[ Free! \ and six! di~uoroalkyl sul_des in high yield ð49JA2531Ł[ Activated haloalkenes\ including penta~uoro!
Sition of hexachloroacetone in DMSO is slower than that of trichloroacetic acid\ but it is accelerated by the addition of water[ It is believed that it is actually the hexachloroacetone hydrate that decomposes into the trichloromethyl anion\ and trichloroacetic acid which in turn decomposes to generate a second trichloromethyl anion ð75JCS"P1#360Ł CCl3 NO2 O2N CCl3CO2H CCl3 NO2 O2N NO2 O2N – DMSO NO2 NO2 NO2 Scheme 28 5[90[3 TRIBROMOMETHYL DERIVATIVES*RBr2 Considerably less work has been carried out on making compounds bearing a tribromomethyl group than on those bearing a trichloromethyl group[ With few exceptions\ the essentials of the methods for making tribromomethyl compounds are the same as those for making the trichloro!