Reactions of polyfluorinated cyclohexadienones with diazoalkanes. Part 1. Formation of cyclopropanes from polyfluorinated cyclohexa-2,4-dienones with diazomethane and phenyldiazomethane

Reactions of polyfluorinated cyclohexadienones with diazoalkanes. Part 1. Formation of cyclopropanes from polyfluorinated cyclohexa-2,4-dienones with diazomethane and phenyldiazomethane Full article

Journal

Journal of the Chemical Society, Perkin Transactions 1
ISSN: 1470-4358

Output data

Year: 2000, Number: 12, Pages: 1929-1933 Pages count : 5 DOI: 10.1039/b001618g

Authors

Kovtonyuk VN , Kobrina LS , Gatilov YV , Bagryanskaya IY , Frohlich R , Haufe G

Affiliations

1	(Данные Web of science) Univ Munster, Inst Organ Chem, D-48149 Munster, Germany
2	(Данные Web of science) NN Vorozhtsov Inst Organ Chem, Novosibirsk 630090, Russia

The reaction of 6-chloro-2,3,4,5,6-pentafluorocyclohexa-2,4-dienone (1) with diazomethane gives a mixture of two diastereoisomers of 6-chloro-3a,4,5,6,7a-pentafluoro-3,3a,6,7a-tetrahydrospiro[indazole-7,2'-oxirane] 2a and 2b. In contrast phenyldiazomethane reacts with polyfluorinated cyclohexa-2,4-dienones 1, 9, and 10 in acetonitrile to form the fluorinated 7-phenylbicyclo[4.1.0]hept-4-en-2-ones 4a,b, 11a,b, and 12a,b as the main products. This reaction shows a remarkable dependence on the polarity of the solvent. While a complex mixture of products was formed in pentane, the reaction in acetonitrile proceeds with high stereoselectivity giving only the two endo-isomers.

Kovtonyuk V. , Kobrina L. , Gatilov Y. , Bagryanskaya I. , Frohlich R. , Haufe G.
Reactions of polyfluorinated cyclohexadienones with diazoalkanes. Part 1. Formation of cyclopropanes from polyfluorinated cyclohexa-2,4-dienones with diazomethane and phenyldiazomethane
Journal of the Chemical Society, Perkin Transactions 1. 2000. N12. P.1929-1933. DOI: 10.1039/b001618g WOS Scopus РИНЦ

Web of science	WOS:000088759600020
Scopus	2-s2.0-0034697718
Elibrary	13337335
OpenAlex	W2019151056