SYNTHESIS OF MONOHALOCYCLOPROPANES AND 1-HALOOLEFINS VIA PHENYL-(DIHALOMETHYL) MERCURY COMPOUNDS

Previous studies of the synthesis of gem-dihalocyclopropanes using C6H5HgCX2Br compounds as CX2 sources were extended to an investigation of the utility of C6H5HgCHXBr compounds in the preparation of monohalocyclopropanes. It was found that both compounds (X=Cl and Br) serve excellently in the prepa...

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Bibliographische Detailangaben
Hauptverfasser:	Seyferth,Dietmar, Simmons,Harry D ,Jr, Singh,Gurdial
Format:	Report
Sprache:	eng
Schlagworte:	ALKENES BROMINE COMPOUNDS BROMINE ORGANIC COMPOUNDS CHEMICAL REACTIONS CHLORINE COMPOUNDS GEM-DIHALOCYCLOPROPANES HALOGENATED HYDROCARBONS HALOMETHYL IONS MERCURY COMPOUNDS MERCURY(II) PHENYL(DIHALOMETHYL) COMPOUNDS MONOCYCLIC COMPOUNDS OLEFINS ORGANOMETALLIC COMPOUNDS PHOSPHINE SILANES SYNTHESIS(CHEMISTRY)
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Beschreibung
Zusammenfassung:	Previous studies of the synthesis of gem-dihalocyclopropanes using C6H5HgCX2Br compounds as CX2 sources were extended to an investigation of the utility of C6H5HgCHXBr compounds in the preparation of monohalocyclopropanes. It was found that both compounds (X=Cl and Br) serve excellently in the preparation of monohalocyclopropanes. A further similarity of C6H5HgCHXBr reagents to C6H5HgCX2Br compounds is seen in their reactions with triethylsilane. A new, general synthesis of vinylic bromides and chlorides based on (dihalomethyl) mercurial chemistry was developed: C6H5HgCHXBr + (C6H5)3P + RR'C=O yields RR'C=CHX + C6H5HgBr + (C6H5)3PO. This general procedure also is applicable to the preparation of olefins of type RR'C=CX2 from aldehydes and ketones. (Extracted) Pub. in Journal of Organometallic Chemistry v3 p337-9 1965 (Copies available only to DDC users).