Trifluoromethyl-p-tolyldiazomethane in 1,3-dipolar cycloaddition reactions |
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Authors: | V V Linev A F Kolomiets A V Fokin |
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Institution: | (1) A. N. Nesmeyanov Institute of Heteroorganic Compounds, Academy of Sciences of the USSR, USSR |
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Abstract: | Trifluoromethyl-p-tolyldiazomethane (I) forms 3+2]-cycloadducts with activated alkenes and alkynes. The products of these regiospecific reactions are substituted pyrazolines (II)–(VI) and pyrazoles (VIII)–(X). Reaction of (I) with fumarates, trifluoropyruvates and allyl chloride is accompanied by elimination of N2 and formation of a 1,2-bis(trifluoromethyl)stilbene. The results obtained indicate that (I) enters only the HOMO-controlled 1,3-dipolar addition reactions.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 7, pp. 1589–1593, July, 1991. |
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