REFERENCES
- For leading references on the preparation of more highly-substituted 2,3-pyridynes and other arynes and hetarynes see: Reinecke M. G. Tetrahedron 1982 38 427 498 van der Plas, H. C.; Roeterdink, F., In The Chemistry of Triple-bonded Functional groups Supplement C; S. Patai and Z. Rappoport, Ed., John Wiley & Sons: Chichester, NY, 1983; pp 421–511. Hart, H., In Supplement C2; The Chemistry of Triple-bonded Functional Groups; S. Patai, Ed.; John Wiley & Sons: Chichester, 1994; Vol. 2; pp 1017–1134.
- Fleet , G. W. J. and Fleming , I. 1969 . J. Chem. Soc. (C) , : 1758 – 1763 . Kurita, J.; Kakusawa, N.; Yasuike, S.; Tsuchiya, T., Heterocycles, 1990, 31, 1937–1940.
- Mallet , M. , Queguiner , G. and Pastour , P. 1972 . Comp. Rend. , 274 : 719 – 722 . Cook, J. D.; Wakefield, B. J., J. Chem. Soc. (C), 1969, 1973–1978.
- Martens , R. J. and den Hertog , H. J. 1962 . Tetrahedron Lett. , : 643 – 645 . Martens, R. J.; den Hertog, H. J., Tetrahedron Lett., 1962, 643–645. Martens, R. J.; den Hertog, H. J., Rec. Trav. Chim. Pays-Bas, 1964, 83, 621–630.
- Walters , M. A. and Shay , J. J. 1995 . Tetrahedron Lett. , 36 : 7575 – 7578 .
- Tsukazaki , M. and Snieckus , V. 1992 . Heterocycles , 33 : 533 – 536 .
- Himeshima , Y. , Sonoda , T. and Kobayashi , H. 1983 . Chemistry Lett. , : 1211 – 1214 .
- Shankaran , K. and Snieckus , V. 1984 . Tetrahedron Lett. , 25 : 2827 – 2830 .
- Effenberger , F. and Daub , W. 1991 . Chem. Ber. , 124 : 2119 – 2125 .
- Purchased from Aldrich.
- Following the procedure of Stang: Stang P. J. Fisk T. E. Synthesis 1979 438 440
- All yields are unoptimized. The cycloaddition reactions gave no other identifiable products other than the anticipated cycloadducts. Apparently, 2,3-pyridyne is much more prone to polymerization than benzyne since reactions involving the latter intermediate usually proceeding in much higher yield. The analytical data for compounds 6, 7, 8, 9, and 11 was identical to that which has been reported previously in the literature.
- Mallet , M. , Queguiner , G. and Pastour , P. 1972 . Comp. Rend. , 274 : 719 – 722 .
- This compound has been prepared previously by another method: Warner V. D. Musto J. D. Turesky S. S. Soloway B. J. Pharm. Sci. 1975 64 1563 1566
- This rearrangement is known to occur in the 4-methoxy analog5 of 10 and in the related adducts formed from the reaction of substituted benzynes with 2-methoxyfuran. Giles R. G. F. Sargent M. V. Sianipar H. J. Chem. Soc. Perkin Trans. 1 1991 1571 1579
- Recent theoretical studies have found that 2,3-pyridyne is less stable than 3,4-pyridyne by 3.2 (BLYP/6–31G*) and 6.0 (B3LYP/6–31G*) kcal/mol. Liu R. Tate D. R. Clark J. A. Moody P. R. Van Buren A. S. Krauser J. A. J. Phys. Chem. 1996 100 3430 3434