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135. Snider, B. B. “Carbofunctionalization of Alkenes” Chemtracts: Org. Chem. 1991, 4, 403-419.
134. Snider, B. B.; Merritt, J. E.; Dombroski, M. A.; Buckman, B. O. “Solvent Effects on Manganese(III)-Based Oxidative Free-Radical Cyclizations: Ethanol and Acetic Acid” J. Org. Chem. 1991, 55, 5544-5553. http://dx.doi.org/10.1021/jo00019a014
Ethanol complements the typical solvent, acetic acid, for Mn(III)-based oxidative free-radical cyclizations. Ethanol acts as a reducing agent for primary radicals, converting them to alkanes. Acetylenes can be used as substrates since the vinyl radicals are reduced to alkenes by ethanol. Finally, a higher percentage of 5-exo cyclization products are obtained in ethanol than in acetic acid.
133. Snider, B. B. “Prins and Carbonyl Ene Reactions” in Comprehensive Organic Synthesis, Vol. 2, B. M. Trost, Editor-in-Chief: Pergamon, Oxford, 1991, pp 527-561. http://dx.doi.org/10.1016/B978-0-08-052349-1.00040-8
132. Snider, B. B. “Ene Reactions with Alkenes as Enophiles” in Comprehensive Organic Synthesis, Vol. 5, B. M. Trost, Editor-in-Chief: Pergamon, Oxford, 1991, pp 1-27. http://dx.doi.org/10.1016/B978-0-08-052349-1.00118-9
131. Snider, B. B.; Merritt, J. E. “Formation of Seven- and Eight-Membered Rings by Manganese(III)-Based Oxidative Free-Radical Cyclization” Tetrahedron 1991, 47, 8663-8678. http://dx.doi.org/10.1016/S0040-4020(01)96189-7
130. Snider, B. B.; Zhang, Q. “Lewis Acid Catalyzed Ene Reactions of α,β-Unsaturated N-Aacyloxazolidinones” J. Org. Chem. 1991, 56, 4908-4913. http://dx.doi.org/10.1021/jo00016a019
129. Curran, D. P.; Morgan, T. M.; Schwartz, C. E.; Snider, B. B.; Dombroski, M. A. “Cyclizations of Unsaturated •CR(COX)2 Radicals. Manganese(III) Acetate Oxidative Cyclizations of Unsaturated Acetoacetates and Atom-Transfer Cyclizations of Unsaturated Haloacetoacetates Give the Same Radicals” J. Am. Chem. Soc. 1991, 113, 6607-6617. http://dx.doi.org/10.1021/ja00017a037
Comparable regio- and stereochemical results were obtained when cyclizations of a series of 2-substituted 3-oxohept-6-enoate (or oct-7-enoate) esters (acetoacetates) were conducted by manganese(II1) acetate oxidation or by iodine or bromine atom transfer cyclization. The observed trends support the conclusion that free radicals (rather than Mn(II1)complexed radicals are involved in the Mn(II1)-mediated oxidative cyclization of tertiary malonates and acetoacetates.
128. Diaz de Delgado, G. C.; Wheeler, K. A.; Snider, B. B.; Foxman, B. M. “Stereospecific, γ-Radiation-Induced Trimerization of Crystalline Sodium trans-2-Butenoate” Angew. Chem., Int. Ed. Engl.1991, 30, 420-422. http://dx.doi.org/10.1002/anie.199104201
127. Snider, B. B.; Allentoff, A. J. “Synthesis of the Bicyclo[5.3.1]undecane Moiety (AB Ring System) of Taxanes” J. Org. Chem. 1991, 56, 321-328. http://dx.doi.org/10.1021/jo00001a060
126. Snider, B. B.; Wan, B. Y. F.; Buckman, B. O.; Foxman, B. M. “Manganese(III)-Based Asymmetric Oxidative Free-Radical Cyclization of Unsaturated β-Keto Sulfoxides” J. Org. Chem. 1991, 56, 328-334. http://dx.doi.org/10.1021/jo00001a061
125. Snider, B. B.; Allentoff, A. J.; Walner, M. B. “Intramolecular [2 + 2] Cycloadditions of Dialkylketenes with Alkenes. Regiochemistry of Intramolecular [2 + 2] Cycloadditions of Ketenes with Alkenes” Tetrahedron 1990, 46, 8031-8042. http://dx.doi.org/10.1016/S0040-4020(01)81460-5
Unsaturated dialkylketenes undergo intramolecular [2 + 2]cycloadditions. Intramolecular cycloadditions of dialkylketenes give higher yields than intramolecular cycloadditions of monoalkylketenes, even though dialkylketenes are less reactive than monoalkylketenes. An intramolecular competition experiment with ketene establishes that trans-alkenes are approximately 33 times more reactive than cis-alkenes in intramolecular cycloadditions.
124. Snider, B. B.; Shi, Z. “Synthesis of Antitumor Cyclic Peroxy Ketals Related to Chondrillin and Xestins A and B” J. Org. Chem. 1990, 55, 5669-5671. http://dx.doi.org/10.1021/jo00309a003
123. Snider, B. B.; Kwon, T. “Oxidative Cyclization of δ,ε- and ε,ζ-Unsaturated Enol Silyl Ethers” J. Org. Chem. 1990, 55, 4786-4788. http://dx.coi.org/10.1021/jo00293a054
122. Snider, B. B.; Yang, K. “Stereo- and Enantiospecific Syntheses of (-)-Reiswigins A and B. Assignment of Absolute and Relative Configuration” J. Org. Chem. 1990, 55, 4392-4399. http://dx.doi.org/10.1021/jo00301a034
121. Snider, B. B.; Kwon, T. “Preparation of Epoxides by Oxidative Decarboxylation of β-Hydroxy Acids. Stereo- and Regiochemistry of Oxidative Elimination of Secondary Radicals with Cupric Acetate” J. Org. Chem. 1990, 55, 1965-1968. http://dx.doi.org/10.1021/jo00293a054
120. Dombroski, M. A.; Kates, S. A.; Snider, B. B. “Manganese(III)-Based Oxidative Free-Radical Tandem and Triple Cyclizations” J. Am. Chem. Soc. 1990, 112, 2759-2767. http://dx.doi.org/10.1021/ja00163a044
119. Kates, S. A.; Dombroski, M. A.; Snider, B. B. “Manganese(III)-Based Oxidative Free-Radical Cyclization of Unsaturated b-Keto Esters, 1,3-Diketones, and Malonate Diesters” J. Org. Chem. 1990, 55, 2427-2436. http://dx.doi.org/10.1021/jo00295a035