Synthesis of 2,7,8-trioxaspiro[4,5]decan-1-ones by manganese(III)-based reaction
Keywords:Manganese(III)-based reaction, spiro bicyclic compound, 1, 2-dioxane ring, γ-lactone ring
Some new spiro bicyclic compounds possessing one 1,2-dioxane ring and one γ-lactone ring were successfully synthesized by manganese(III)-based reaction of 1,1-diarylethenes and 2-acetylbutyrolactone under air. The procedure was simple and the product yield was high. The NMR spectrometric features of the products were analyzed and the reaction mechanism is briefly discussed.
Keywords. Manganese(III)-based reaction, spiro bicyclic compound, 1,2-dioxane ring, γ-lactone ring.
(a) L. Zhang, W. S. Zhou, X. X. Xu. A new sesquiterpene peroxide (yingzhaosu C) and sesquiterpenol (yingzhaosu D) from Artabostrys unciatus (L.) Meer., J. Chem. Soc., Chem. Commun., 8, 523-524 (1988). (b) D. A. Casteel. Peroxy natural products, Nat. Prod. Rep., 16(1), 55-73 (1999).
Forexample: (a) S. E. Kiruthika, R. Amritha, P. T. Peramal. An Efficient Strategy for Functionalized Spirolactones and Dispirodihydrofuranyl Oxindoles Using Amines and Activated Alkynes, Tetrahedron Lett., 53(26), 3268-3273 (2012). (b) J. R. Syu, C. H. Lin, C. W. Kuo, D. Y. Yan. Synthesis of Benzofuran-containing Spirolactones from Diarylcyclopropenones, Tetrahedron Lett., 55(6), 1207-1211 (2014). (c) Niharika, P., Satyanarayana, G., One-pot C=C/C=O bond formation. Synthesis of spirocyclic Lactones, RSC. Adv., 6, 837-843 (2016).
(a) J. Yoshida, K. Sakaguchi, S. Isoe, K. Hirotsu. Electro-initiated [2+2+2] cycloaddition of molecular oxygen, olefin, and 1,3-diketone, Tetrahedron Lett., 28(6), 667-670 (1987). (b) J. Yoshida, S. Nakatani, K. Sakaguchi, S. Isoe. Formal [2+2+2] cycloaddition of molecular oxygen, 1,3-diketone, and olefin. Synthesis and reactions of cyclic peroxides, J. Org.
Chem., 54(14), 3383-3389 (1989).
S. Tategami, T. Yamada, H. Nishino, J. D. Korp, K. Kurosawa. Formation of 1,2-dioxacyclohexanes by the reaction of alkenes with tris(2,4-pentanedionato)manganese(III) or with β-keto carbonyl compounds in the presence manganese(III) acetate, Tetrahedron Lett., 31(44), 6371-6374 (1990).
T. Yamada, Y. Iwahara, H. Nishino, K. Kurosawa. Manganese(II)- and (III)-mediated Free-radical Cyclization of Alkenes, β-Keto Esters and Molecular Oxygen, J. Chem. Soc. Perkin Trans., 1(5), 609-616 (1993).
T.-T. Huynh, V.-H. Nguyen, H. Nishino. One-pot synthesis of 2-oxa-7-azaspiro[4.4]nonane-8,9-diones using Mn(III)-based oxidation of 4-acylpyrrolidine-2,3-diones, Tetrahedron Lett., 58(37), 3619-3622 (2017).
E. I. Heiba, R. M. Dessau, W. J. Koehl. Oxidation by
Metal Salts. III. The Reaction of Manganese Acetate with Aromatic Hydrocarbons and the Reactivity of the Carboxymethyl Radical, J. Am. Chem. Soc., 91, 138-145 (1969).
A. Klages. Synthesis of Arylated Ethylenebenzenes, Ber., 35, 2646-2649 (1902).
(a) W. E. Fristad, J. R. Peterson, A. B. Ernst, G. B. Urbi G. Mechanisms for Manganese(III) Oxidations with Alkenes, Tetrahedron, 42(13), 3429-3442(1986). (b) B. B. Snider, R. Mohan, S. A. Kates. Manganese(III) Based Oxidative Free Radical Cyclizations .2. Polycyclization Reactions Proceeding Through Tertiary Cations, Tetrahedron Lett., 28(1), 841-844 (1987).
H. Nishino, V.-H. Nguyen, S. Yoshinaga, K. Kurosawa. Formation of Tetrahydrofuran Derivatives and Acetonylation of Alkenes Using CarbonRadicals Derived from Manganese(III) Oxidation of Diketene, J. Org. Chem., 61(23), 8264-8271 (1996).