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By Alan R. Katritzky

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F. Weygand and K. Burger, Chem. Ber. 99, 2880 (1966). W. Carpenter, A. Haymaker. and D. W. Moore, J. Org. Chem. 31, 789 (1966). W. P. Norris and W. G. Finnigan, J. Urg. Chem. 31,3292 (1966). I. L . Knunyants and Yu. V. Zeifman, Bull. Acad. Sci. USSR, Diu. Chem. Sci. (Engl. ), 695 (1967). G. M. Brooke and M. Abul Quasem, J. Chem. Soc. C , 865 (1967). G. M. Brooke and B. S. Furnies, J. Chem. C, 869 (1967). G. M. Brooke and R. J . D. Rutherford, J. Chem. S O C . C , 1 I89 ( 1967). Y. V. Zeifman, N .

OH R' = H, C02Me SCHEME 71 A spiro adduct is the result of the reaction of diazofluorene and perfluoro-2-butyne (72AG(E)224, 72TL3479; 74CB2027). With diazomethane and ethyl diazoacetate the above-mentioned trifluoromethyl-substituted alkynylamino and alkynyl hydroxy acid esters give a single [3 + 21 cycloadduct, namely the 2-(3-pyrazolyl)-3,3,3-trifluoroalanineand the 2-(3pyrazolyl)-3,3,3-trifluorolacticacid derivatives, respectively (92LA947) (Scheme 71). Azides rapidly react with electron-poor alkynes to give 1,2,3-triazoles (84M15).

Hutchinson, and G. Whittaker. S. Perkin Trans. I . 214 (1979). R. Fields and J. P. Tomlinson, J . Fluorine Chem. 13, 147 (1979). H. Kimoto and L. A. Cohen, J . Org. Chem. 44, 2902 (1979). A. A . Mel’nikov, M. M. Sokolova. M. A . Pervozvanskaya. and V. V. Mel’nikov, J . Org. Chum. USSR ( E n g l . ) 15, 1677 i1979). G . F. ll’in, A. F. Kolomiets, and G . A. Sokol’skii, J . Org. Chem. USSR (EngI. ) 15, 2008 (1979). L. A. Lazukina and V. P. Kukhar’. J . Org. Chem. USSR (Engl. ) 15, 2009 (1979). K.

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