Download e-book for iPad: Ring Enlargement in Organic Chemistry by Manfred Hesse

By Manfred Hesse

ISBN-10: 0895739917

ISBN-13: 9780895739919

ISBN-10: 3527281827

ISBN-13: 9783527281824

Ring expansion reactions are vital not just for the synthesis of typical compounds and prescribed drugs but in addition for his or her significant position in natural synthesis. This publication summarizes the method of ring growth of heteroatom jewelry. The 9 chapters are prepared in response to response variety, allowing quick access to the knowledge.

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67] S. N. Moorthy, R. Vaidyanathaswamy, D. Devaprabhakara, Synthesis 1975, 194. [68] G. H. Whitham, M. Commun. 1967, 294. [69] P. G. J. Chem. 53, 5576 (1988). [70] E. Fouque, G. Rousseau, Synthesis 1989, 661. M. Trost, W. C. Vladuchick, Synthesis 1978, 821. [72] H. H. Wasserman, R. E. S. Soc. 91, 2376 (1969). M. Beccalli, A. Marchesini, H. Molinari, Tetrahedron Lett. 27, 627 (1986). [74] S. Senda, K. Hirota, T. Asao, Y. Yamada, Tetrahedron Lett. 26, 2295 (1978). [75] J. A. Miller, G. M. Commun.

A concerted reaction takes place: Loss of water and migration of the alkyl residue anti to the leaving group. The lactam is formed by addition of water to the intermediate carbocation. To illustrate the Beckmann rearrangement, some examples are given in Scheme 11/19. g. ref. [87]. 11/118 11/119 o 11/120 H20 © N-Cf 11/122 N=C^ 11/121 Scheme 11/18. Mechanism of the Beckmann rearrangement of cycloalkanone. 9) For a review with respect to bicyclic oximes see ref. [81]. 10) Reagents used in the Beckmann rearrangement are phosphorous [90], formic acid [88], liquid SO2, P(C6H5)3)-CC14, hexamethylphosphorous acid triamide, 2-chloropyridinium fluorosulfonate, SOC12, silica gel, P2O5-methanesulfonic acid, HCl-HOAc-Ac2O, polyphosphoric acid [89] as well as trimethylsilyl polyphosphate [88], hydrochloric acid [88], p-toluenesulfonyl chloride [88], trimethylsilyl trifluoromethane sulfonate [93].

Subsequently, intramolecular electrophilic attack on the allylic bond, and C-O bond cleavage leads to product IV/9 [2]. CHjO, 138° 1h CH3O' IV/7 IV/6 C6H5 76 7. Scheme IV/2. Thermal cyclobutenone —» benzoquinone transformation involving an allyl group migration [2]. IV1. Ring Expansion from Four-membered Rings 0 55 0 CH3O 0 V 0 CON(i-Pr)2 IV/12 (67%) OCH3 IV/11 (89%) IV/10 (72%) I L] CH3O 11 0 IV/13 (92%) >,b CH3O H9C4 IV/14 (84%) 1 1 \s OH IV/15(94%) IV/16 Scheme IV/3. Some examples of quinones from 4-aryl-(or heteroaryl)-4-hydroxybutenones [1] [2] and [3] [4].

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Ring Enlargement in Organic Chemistry by Manfred Hesse

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