Novel 1:1 adducts from the reaction of hexafluoroacetone azine with various olefins and 1,3-dienes; Diels-Alder adducts as intermediates in the formation of criss-cross 2:1 adducts |
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Authors: | Stuart E. Armstrong Anthony E. Tipping |
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Affiliation: | Department of Chemistry, University of Manchester Institute of Science and Technology, Manchester M60 IQD Gt. Britain |
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Abstract: | Hexafluoroacetone azine1 (I) has been reported2,3 to react thermally (160–180°) with electron-rich olefins of type H2CCHR (R H, Me, or Et) to give “criss-cross” (1,3-:4,2-) adducts (II). In contrast, cis- or trans-but-2-ene and cyclohexene react under comparable conditions to give nitrogen and products derived formally from addition and insertion reactions of bis(trifluoromethyl)-carbene, although it is doubtful if the free carbene is involved2,4. The reaction of azine (I) with alkanes is reported5 to involve a radical mechanism in which the diazo compound (CF3)2CN2, and thence the carbene (CF3)2C:, is formed by a secondary process. |
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