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ABSTRACT

The authors have studied the effect of a magnetic field on Baldwin’s rules. The authors have proposed a new mechanism that takes into account the effect of the angle and energy endo- or exo-cyclization. The authors propose to extend the rule Bouldwin not only for sp3-, sp2- and sp- orbits, but and for d1 - d10 and f1 - f14 elements of I-VIII of the Periodic table.

KEYWORDS

Magnetic field, mechanism of the Baldwin’s rule, endo- or exo-cyclization.

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References

[1] Baldwin, J. E. 1976. “Rules for Ring Closure.” J. Chem. Soc. Chem. 18: 734.

[2] Baldwin, J. E., Thomas, R. C., Kruse, L, I., and Silberman, L. 1978. “Rules for Ring Closure: Ring Formation by Conjugate Addition of Oxygen Nucleophiles.” J. Org. Chem. 42 (24): 3846.

[3] Gilmore, K., and Alabugin, I. V. 2011. “Cyclizations of Alkynes: Revisiting Baldwin’s Rules for Ring Closure.” Chem. Rev. 111: 6513-56.

[4] Alabugin, I., Gilmore, K., and Manoharan, M. 2011. “Rules for Anionic and Radical Ring Closure of Alkynes.” J. Am. Chem. Soc. 133: 12608-23.

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[6] Lin, G. Y., Yang, C. Y., and Liu, R. S. 2007. “Gold-Catalyzed Synthesis of Bicyclo[4.3.0]nonadiene Derivatives via Tandem 6-endo-dig/Nazarov Cyclization of 1,6-Allenynes.” J. Org. Chem. 72: 6753-7.

[7] Overhand, M., and Hecht, S. M. 1994. “A Concise Synthesis of the Antifungal Agent (+)-Preussin.” Journal of Organic Chemistry 59 (17): 4721-2.

[8] Baldwin, J. E., and Kruse, L. I. 1977. “Rules for Ring Closure. Stereoelectronic Control in the Endocyclic Alkylation of Ketone Enolates.” Journal of the Chemical Society 7: 233.

[9] Baldwin, J. 1982. “Rules for Ring Closure: Application to Intramolecular Aldol Condensations in Polyketonic Substrates.” Tetrahedron 38 (19): 2939.

[10] Baldwin, J. E., Cutting, J., Dupont, W., Kruse, L., Silberman, L., Thomas, R. C. 1976. Rules for Ring Closure. J. Chem. Soc., Chem. Commun., 736-8.

[11] Alabugin, I. V., and Gilmore, K. 2013. “Finding the Right Path: Baldwin “Rules for Ring Closure” and Stereoelectronic Control of Cyclizations.” Chem. Commun. 49: 11246-50.

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