Download PDF by Solmon P.H., Miller A.: Writing Reaction Mechanisms in Organic Chemistry

By Solmon P.H., Miller A.

ISBN-10: 0124967124

ISBN-13: 9780124967120

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6, 29 (1975) [CA 83, 8773p ( 1975)). 26 [Sec. H MICHAEL P. SAMMES AND ALAN R. KATRITZKY 2. Il8 Hypobromite oxidation of 97 leads to the same compound’29(Scheme 3 9 , whereas the 4-bromo analog of 96 has been prepared by base elimination of HBr from a dibromopyrazoline N,N’-dioxide p r e c u r ~ o r . ” ~ /Me M e n M e C,H,,ONO, ACOH Me NOH “+OH Me Me N

MISCELLANEOUS METHODS 1. PNMe Me "' Giz Meo KOH e 53% (72) (71) SCHEME 26 2 . "' D. P. G . Hamon and L. J. S. Chem. , 1330 (1970). G . , 1665 (1963). 'I4 M. Lempert-Srtter and K. Lempert, Tetrahedron 31, 1677 (1975). 'I' S. D. Andrews, A. C. Day, and R. N. Inwood, J. Chem. SOC. C , 2443 (1969). 'I6 P. Bouchet, J. Elguero, R. Jacquier, and F. Forissier, C. R. Acad. , Ser. C 269, 570 (1 969). C. Wentrup and W. D. Crow, Tetrahedron 27, 361 (1971). 'I3 Sec. G] 23 THE 3H-PYRAZOLES 1 (73) SCHEME 27 G .

A m . Chem. 85, 1273 (1963). S. Mataka, T. Ohshirna, and M. Tashiro, J. Heterocycl. Chem. 19, 65 (1982). R. Baurnes, J . Elguero, R. , 3781 (1973). Sec. A] 33 THE 3H-PYRAZOLES ,CO,Me Type A P h d Ph~ A or H2S0,. 25 C N 90,Me Ph Q N H Ph CI CI SCHEME 41 Me0,C C0,Me Ph C0,Me A Ph E Ph N XG? 14’ 34 [Sec. A MICHAEL P. SAMMES AND ALAN R. 70*80n142,143 a. The Mechanism of the Reaction. Formation of the three types of products has been accommodated in terms of competitive suprafacial [I ,5]-shifts by a substituent at C-3 (Scheme 43).

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