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Get Advances in Cycloaddition. Volume 5 PDF

By M. Harmata

ISBN-10: 0080546382

ISBN-13: 9780080546384

ISBN-10: 0762303468

ISBN-13: 9780762303465

The improvement and alertness of cycloaddition method is still on the vanguard of analysis in artificial natural chemistry. This quantity starts with a overview of tools to be had for the synthesis of 7-membered earrings and is with paintings on metal-catalyzed cycloadditions. there's then an replace at the cycloaddition chemistry of 2-pyrone, after which a distinct program of photocycloaddition is special. the ultimate bankruptcy is a dialogue of the newest explorations of the response of rhodium-stabilized vinyl carbenoids with dienes.

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Gazz. Chim. Ital. 1986, 116, 109. 64. ; Wiley: New York, 1987; Parts 1 and 2. Schleyer, Pv. ; Buss, V. J. Am. Chem. Soc. 1969, 91, 5880-5882. ; Harch, P. ; Taft, R. ; Hehre, W. J. Am. Chem. Soc. 1975, 97, 2902-2904. 65. ; Breuer, E. J. Am. Chem. Soc. 1959, 6522-6523. 66. Pasto, D. ; Chen, A. J. Am. Chem. Soc. 1973,95, 1553. Pasto, D. ; Chen, A. E-T. Tetrahedron Lett. 1973, 713. , unpublished results. 67. Fowler, E W. Angew. , Int. Ed. Engl. 1971, 10, 135. 68. ; Ugi, I. Angew. , Int. Ed. Engl. 1985, 24, 594.

Am. Chem. Soc. 1985, 107, 7771. 22. ; Yamakawa, K. Tetrahedron Lett. 1992, 33, 7545. 23. Katritzky, A. ; Seryduk, L. J. Am. Chem. Soc. 1995, 117, 12015. 24. Banwell, M. ; Cameron, J. M. Tetrahedron Lett. 1996, 37, 525. 25. Wolfe, M. ; Aube, J. J. Org. Chem. 1997, 62, 654. 26. Wovkulich, P. M. In Comprehensive Organic Synthesis; Trost, B. ; Pergamon: Oxford, 1991, Vol. 1, Chap. 3. 27. Berson, J. ; Jones, M. J. Am. Chem. Soc. 1964, 86, 5017. Berson, J. ; Gajewski, J. J. J. Am. Chem. Soc. 1964, 86, 5019.

The reaction is relatively insensitive to substitution of the alkyne terminus. Terminal alkynes and internal alkynes with electron-rich, electron-poor, sterically demanding, and conjugating substituents all provide good to excellent yields of the 5,7-fused bicyclic products (Table 2). Only in the case of 31a is the isolated yield low because of the difficulties handling the more volatile product. The cycloaddition proceeds efficiently even with methyl substitution of the double bond of the vinylcyclopropane.

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Advances in Cycloaddition. Volume 5 by M. Harmata


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