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1 For some reviews: (a) Boger, D. L. Tetrahedron 1983, 39, 2869-2939.
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Boger, D.L.1
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(b) Boger, D. L. Chem. Rev. 1986, 86, 781-793.
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Boger, D.L.1
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3
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Hetero diels-alder methodology in organic synthesis
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Academic: New York
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(c) Boger, D. L.; Weinreb, S. M. Hetero Diels-Alder Methodology in Organic Synthesis; Oganic Chemistry Monograph Series, Vol. 47; Academic: New York, 1987.
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Oganic Chemistry Monograph Series
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Boger, D.L.1
Weinreb, S.M.2
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0001101712
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2 (a) Benson, S. C.; Palabrica, C. A.; Snyder, J. K. J. Org. Chem. 1987, 52, 4610-4614.
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J. Org. Chem.
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Benson, S.C.1
Palabrica, C.A.2
Snyder, J.K.3
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5
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0001206433
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(b) Benson, S. C.; Gross, J. L.; Snyder, J. K. J. Org. Chem. 1990, 55, 3257-3269.
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J. Org. Chem.
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Benson, S.C.1
Gross, J.L.2
Snyder, J.K.3
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6
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(c) Benson, S. C.; Lee, L.; Snyder, J. K. Tetrahedron Lett. 1996, 37, 5061-5064.
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Tetrahedron Lett.
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Benson, S.C.1
Lee, L.2
Snyder, J.K.3
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10
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37049092813
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5 Other reports of indoles as dienophiles in Diels-Alder reactions, see ref. 2b, citations 4 and 5, ref. 2c, citation 1, also: (a) Gilchrist, T. L.; Lingham, D. A.; Roberts, T. G. J. Chem. Soc., Chem. Comm. 1979, 1089-1091.
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J. Chem. Soc., Chem. Comm.
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Gilchrist, T.L.1
Lingham, D.A.2
Roberts, T.G.3
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12
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0002248324
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(c) Pindur, U.; Pfeuffer, L.; Kim, M.-H. Helv. Chim. Acta 1989, 72, 65-72.
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Helv. Chim. Acta
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Pindur, U.1
Pfeuffer, L.2
Kim, M.-H.3
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0025688692
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(d) Oishi, E.; Taido, N.; Iwamoto, K.; Miyashita, A.; Higashino, T. Chem. Pharm. Bull. 1990, 38, 3268-3272.
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Oishi, E.1
Taido, N.2
Iwamoto, K.3
Miyashita, A.4
Higashino, T.5
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14
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(e) Gieseler, A.; Steckhan, E.; Wiest, O.; Knoch, F. J. Org. Chem. 1991, 56, 1405-1411.
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Gieseler, A.1
Steckhan, E.2
Wiest, O.3
Knoch, F.4
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16
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37049085571
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(g) Nesi, R. Giomi, D.; Turchi, S.; Falai, A. J. Chem. Soc., Chem. Comm. 1995, 2201-2202.
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Nesi, R.1
Giomi, D.2
Turchi, S.3
Falai, A.4
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17
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0000702147
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6 Other reports of pyrroles as dienophiles in Diels-Alder reactions, see ref. 3, citations 4-6, ref. 5g, also: (a) Wenkert, E.; Moeller, P. D. R.; Piettre, E. R. J. Am. Chem. Soc. 1988, 110, 7188-7194.
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Wenkert, E.1
Moeller, P.D.R.2
Piettre, E.R.3
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(b) Heine, H. W.; LaPorte, M. G.; Overbaugh, R. H.; Williams, E. A. Heterocycles 1995, 40, 743-752.
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Heine, H.W.1
LaPorte, M.G.2
Overbaugh, R.H.3
Williams, E.A.4
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20
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0018014483
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7 Other reports of imidazoles as dienophiles in Diels-Alder reactions: (a) Seitz, G.; Kaepmchen, T. Arch. Pharm. (Weinheim) 1978, 311, 728-735.
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Arch. Pharm. (Weinheim)
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Seitz, G.1
Kaepmchen, T.2
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(b) Seitz, G.; Hoferichter, R.; Mohr, R. Arch. Pharm. (Weinheim) 1989, 322, 415-417.
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Arch. Pharm. (Weinheim)
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Seitz, G.1
Hoferichter, R.2
Mohr, R.3
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(c) Xu, Y.-Z.; Yakushijin, K.; Horne, D. A. Tetrahedron Lett. 1993, 34, 6981-6984.
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Tetrahedron Lett.
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Xu, Y.-Z.1
Yakushijin, K.2
Horne, D.A.3
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23
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84988099599
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8 For a discussion of intramolecular inverse electron demand Diels-Alder reactions with 1,2,4-triazines: Taylor, E. C. Bull. Soc. Chim. Belg. 1988, 97, 599-613.
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Bull. Soc. Chim. Belg.
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Taylor, E.C.1
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9 Benson, S. C.; Li, J.-H.; Snyder, J. K. J. Org. Chem. 1992, 57, 5285-5287
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J. Org. Chem.
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Benson, S.C.1
Li, J.-H.2
Snyder, J.K.3
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25
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0029143822
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10 Fan, W.-H.; Parikh, M.; Snyder, J. K. Tetrahedron Lett. 1995, 36, 6591-6594.
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Tetrahedron Lett.
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Fan, W.-H.1
Parikh, M.2
Snyder, J.K.3
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27
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0003600435
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Wiley-Interscience: New York
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12 For reviews of triazine syntheses: (a) Neunhoeffer, H. Chemistry of 1,2,3-Triazines and 1,2,4-Triazines, Tetrazines, and Pentazines: Wiley-Interscience: New York, 1978; 194-200.
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Chemistry of 1,2,3-Triazines and 1,2,4-Triazines, Tetrazines, and Pentazines
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Neunhoeffer, H.1
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28
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84944078040
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Katritzky, A. R.; Rees, C. W.; Boulton, A. J.; McKillop, A., Eds.; Pergamon, Oxford
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(b) Neunhoeffer, H. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R.; Rees, C. W.; Boulton, A. J.; McKillop, A., Eds.; Pergamon, Oxford, 1984; Vol. 3, pp 385-456.. Previous preparation of 4(H)-5,6-diphenyl-1,2,4-triazin-3-thione:
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(1984)
Comprehensive Heterocyclic Chemistry
, vol.3
, pp. 385-456
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Neunhoeffer, H.1
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29
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37049049391
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(c) Sadler, P. W. J. Chem. Soc. 1961, 243-246. Previous preparation of 4(H)-5-phenyl-1,2,4-triazin-3-thione:
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J. Chem. Soc.
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Sadler, P.W.1
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31
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84920294683
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note
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13C NMR, IR, and LR and HRMS.
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32
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0342724871
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Oae, S., Ed.; Plenum: New York; Chapter 10
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14 (a) Truce, W. E.; Klingler, T. C.; Brand, W. W. In Organic Chemistry of Sulfur: Oae, S., Ed.; Plenum: New York, 1977; Chapter 10.
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Organic Chemistry of Sulfur
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Truce, W.E.1
Klingler, T.C.2
Brand, W.W.3
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0010553392
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Jones, D. N., Ed.; Pergamon: New York
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(b) Durst, T. In Sulphur, Selenium, Silicon, Boron, Organometallic Compounds; Comprehensive Organic Chemistry: The Synthesis and Reactions of Organic Compounds, Vol. 3; Jones, D. N., Ed.; Pergamon: New York, 1979; pp 183-184.
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In Sulphur, Selenium, Silicon, Boron, Organometallic Compounds; Comprehensive Organic Chemistry: The Synthesis and Reactions of Organic Compounds
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, pp. 183-184
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Durst, T.1
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34
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0000375013
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15 Analogous to decarboxylation, desulfination of a β-carbonyl sulfinic acid should be very facile: (a) Stirling, C. J. M. Int. J. Sulfur Chem. 1971, 6, 277-320.
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Int. J. Sulfur Chem.
, vol.6
, pp. 277-320
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Stirling, C.J.M.1
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35
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0010556552
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Patai, S., Ed.; Wiley & Sons: New York; Chapter 1
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(b) Stirling, C. J. M. In The Chemistry of Sulphinic Acids, Esters, and Their Derivatives; Patai, S., Ed.; Wiley & Sons: New York, 1990; Chapter 1.
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Stirling, C.J.M.1
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36
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0010627233
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16 Thermal desulfination of alkyl sulfinic acids is thought to precede by a radical pathway: Wellisch, E.; Gipstein, E.; Sweating, O. J. J. Org. Chem. 1962, 27, 1810-1812.
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J. Org. Chem.
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Wellisch, E.1
Gipstein, E.2
Sweating, O.J.3
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38
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18 Powers, J. C.; Meyer, W. P.; Parsons, T. G. J. Am. Chem. Soc. 1967, 89, 5812-5820.
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J. Am. Chem. Soc.
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Powers, J.C.1
Meyer, W.P.2
Parsons, T.G.3
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39
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84920294682
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note
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19 From the MSDS, bromoacetyl bromide is highly corrosive, a potent lachrymator and "extremely destructive to tissue of the mucous membranes and upper respiratory tract, eyes, and skin."
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