Comprehensive Organic Functional Group Transformations, by Alan R. Katritzky, Otto Meth-Cohn, and Charles W. Rees

By Alan R. Katritzky, Otto Meth-Cohn, and Charles W. Rees (Editors-in-Chief)

An unlimited variety of alternative practical teams is almost certainly 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 useful teams and to spotlight those who are little recognized or unknown. All attainable mixtures of heteroatoms were surveyed, apart from complexes within which carbon atoms are bonded in simple terms to transition components. the cloth is organised in 4 elements: tetracoordinated carbon atoms bearing 3 hooked up heteroatoms are coated partially 1, and people bearing 4 heteroatoms partly II; the synthesis of tricoordinated carbonatoms with 3 hooked up heteroatoms is defined partially III; stabilized radicals and carbocations with 3 connected heteroatoms are lined in brief partly IV.

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Extra info for Comprehensive Organic Functional Group Transformations, Volume 6 (Synthesis: Carbon with Three or Four Attached Heteroatoms)

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Diselenane "Scheme 16# ð51JOC2473Ł[ Tetra~uoroethylene also reacts with tetraselenium bis"hexa~uoroarsenate"V## over extended periods of time to yield bis"per~uoroethyl# diselenide in good yield "Scheme 16# ð66CJC2025Ł[ Similar reactions have been perfomed using Se7"AsF5#1\ and Se7"Sb1F00#1\ which both react with tetra~uoroethylene to give the bis"per~uoroethyl# diselenide in nearly quantitative yield ð62JCS"D#1203Ł[ Reaction of selenium metal with tri~uoroiodomethane results in the formation of bis"tri~uoromethyl# mono!

Hydes[ In a similar reaction\ anhydrides react to give tribromolactols or their tautomeric keto acids ð56JOC1055Ł[ Tribromomethyl carbinols are also obtained when\ in the presence of aldehydes\ tribromoacetic acid decarboxylates in DMSO ð72CC172\ 73JCS"P1#0136Ł\ or a mixture of the acid and its sodium salt decarboxylates in DMF ð81TL2324Ł[ Again corresponding to the trichloromethyl case\ the reaction between tributyl"tribromo! methyl#stannane and an aldehyde gives a tribromomethyl carbinol[ The main di}erence between the two reactions is that tribromomethylation is exothermic at room temperature whereas trichloro!

And six! di~uoroalkyl sul_des in high yield ð49JA2531Ł[ Activated haloalkenes\ including penta~uoro! 1H! sulfonyl ~uorides "Scheme 12# ð75ZOR0723Ł[ "vii# From carbon disul_de Treatment of carbon disul_de with elemental ~uorine at −019>C is reported to yield octa~uoro! diselenane "Scheme 16# ð51JOC2473Ł[ Tetra~uoroethylene also reacts with tetraselenium bis"hexa~uoroarsenate"V## over extended periods of time to yield bis"per~uoroethyl# diselenide in good yield "Scheme 16# ð66CJC2025Ł[ Similar reactions have been perfomed using Se7"AsF5#1\ and Se7"Sb1F00#1\ which both react with tetra~uoroethylene to give the bis"per~uoroethyl# diselenide in nearly quantitative yield ð62JCS"D#1203Ł[ Reaction of selenium metal with tri~uoroiodomethane results in the formation of bis"tri~uoromethyl# mono!

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