Reaction of Hydroximic Chlorides with Hexabutylditin. A Mild Method for Generation and Cycloaddition of Nitrile Oxides

References

• Huisgen , R. and Mack , W. 1961 . Tetrahedron Lett. , : 583
   Web of Science ®Google Scholar
• Curran , D. P. and Kim , B. H. 1986 . Synthesis , : 312
   Google Scholar
• Huisgen , R. 1963 . Angew. Chem., Int. Ed. Engl. , 2 : 565
   Google Scholar
• Grundmann , C. and Grünanger , P. 1971 . The Nitrile Oxides , Berlin : Springer-Verlag .
   Google Scholar
• Caramella , P. and Grünanger , P. 1984 . 1,3-Dipolar Cycloaddition Chemistry , Edited by: Padwa , A. 291 New York : John Wiley and Sons .
   Google Scholar
• Beltrame , P. , Dondoni , A. , Barbaro , G. , Gelli , G. , Loi , A. and Steffè , S. 1978 . J. Chem. Soc., Perkin Trans. , 2 : 607
   Google Scholar
• Mukaiyama , T. and Hoshino , T. 1960 . J. Am. Chem. Soc. , 82 : 5339
   Web of Science ®Google Scholar
• Compound 3a: mp 39–41 °C; 1H NMR (300 MHz, CDC13) δ 8.12–7.94(2 H, m), 7.78–7.64(2 H, m), 7.60–7.31(6 H, m), 4.35(1 H, m), 2.80(1 H, m), 2.07(1 H, m), 1.82–0.84(7 H, m); 13C NMR(75 MHz, CDC13) δ 157.6, 130.7, 129.1, 128.8, 128.7, 128.4, 128.2, 127.8, 127.0, 111.5, 77.1, 52.2, 25.5, 25.1, 24.3, 19.9; IR(neat) 3030, 1350, 945 cm−1; MS, m/e 320(M+), 238, 105; HRMS, calcd for C20H20N2O2 320.1524, found 320.1485
   Google Scholar
• Compound 4a: 1H NMR (300 MHz, CDC13) δ 8.03–7.91(2 H, m), 7.73–7.62(2 H, m), 7.50–7.30(6 H, m), 4.07(1 H, m), 2.84(1 H, m), 1.82–0.92(8 H, m), 0.86(3 H, t, J = 6.6 Hz), 0.76(3 H, t, J = 6.6 Hz); IR (neat) 2959, 1449, 1347, 928, 758 cm−1; MS, m/e 350(M+), 320, 238, 105; HRMS, calcd for C22H26N2O5 350.1994, found 350.1963, calcd for C22H26NO(M-NO) 320.2015, found 320.2016
   Google Scholar
• Cunico , R. F. and Bedell , L. 1983 . J. Org. Chem. , 48 : 2780
   Google Scholar
• Albini , F. M. , Vitali , D. , Oberti , R. and Caramella , P. 1980 . J. Chem. Research(S) , : 348
   Google Scholar
• Gilman , H. , Atwell , W. H. and Cartledge , F. K. 1966 . Adv. Organometal. Chem. , 4 : 1
   Web of Science ®Google Scholar
• Barker , P. J. , Davies , A. G. , Hawari , J. A. and Tse , M. W. 1980 . J. Chem. Soc., Perkin Trans. 2 , : 1488
   Google Scholar
• Cooper , J. , Hudson , A. and Jackson , R. A. 1973 . J. Chem. Soc., Perkin Trans. 2 , : 1056
   Google Scholar
• Sawyer , A. K. 1972 . Organotin Compounds , Edited by: Sawyer , A. K. New York : Marcel Dekker, Inc. .
   Google Scholar