Publications 1970-1977

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26.        Snider, B. B.; Brown, L. A.; Conn, R. S. E.; Killinger, T. A. “The Lewis Acid Catalyzed Reaction of 3-Butyn-2-one with Alkenes” Tetrahedron Lett. 1977, 2831-2834.


25.        Snider, B. B.; Hrib, N. J. “A Synthesis of Inside-Inside Bicyclics. A One Step Synthesis of [10]-Paracyclophanes” Tetrahedron Lett. 1977, 1725-1728.


24.       Breslow, R.; Corcoran, R. J.; Snider, B. B.; Doll, R. J.; Khanna, P. L.; Kaleya, R. “Selective Halogenation of Steroids Using Attached Aryl Iodide templates” J. Am. Chem. Soc. 1977, 99, 905-915.

23.       Snider, B. B.; Hrib, N. J.; Fuzesi, L. “Allylic Cyanobis(methylthio)methylation. Insertion of a Functionalized Carbon in an Allylic Carbon-Hydrogen Bond” J. Am. Chem. Soc. 1976, 98, 7115-7117.


22.       Snider, B. B. “The Stereospecific Aluminum Chloride Catalyzed [2 + 2] Cycloaddition of Propiolate Esters with Unactivated Alkenes” J. Org. Chem. 1976, 41, 3061-3062.

The aluminum chloride catalyzed reaction of alkenes with propiolate esters at 25 °C produces either ene adducts and/or stereospecific {2 + 2] cycloadducts depending on the substitution pattern of the alkene.

21.       Snider, B. B.; Corcoran, R. J.; Breslow, R. “Removal of the Steroid Side Chain Using Remote Oxidation. Conversion of 3b-Cholestanol to Androsterone Acetate” J. Am. Chem. Soc. 1975, 97, 6580-6581.

20.      Salamone, J. C.; Taylor, P.; Snider, B.; Israel, S. C. “Copolymerization Behavior of Vinylimidazolium Salts” J. Polym. Sci., Polym. Chem. Ed. 1975, 13, 161-170.

Copolymerization studies of cationic monomers have been reported in the literature to yield wide variations in reactivity ratios and Qe values, depending on the comonomer and the nature of the solvent. In this work are presented the copolymerization characteristics of a variety of vinylimidazolium salts in both water and ethanol solution. From these studies, the effect of solvent polarity, of substitution at the imidazolium 2-position, of the type of counterion, and of the hydrophilic–hydrophobic character of the monomeric salts could be ascertained. The results of the study are consistent with other related investigations, in that solvent polarity and comonomer both strongly affected copolymerization.

19.       Breslow, R.; Snider, B. B.; Corcoran, R. J. “Cortisone Synthesis Using Remote Oxidation” J. Am. Chem. Soc. 1974, 96, 6792-6794.

18.       Breslow, R.; Corcoran, R. J.; Snider, B. B. “Remote Functionalization of Steroids by a Radical Relay Mechanism” J. Am. Chem. Soc. 1974, 96, 6791-6792.

16.       Corey, E. J.; Snider, B. B. “Preparation of an Optically Active Intermediate for the Synthesis of Prostaglandins” J. Org. Chem. 1974, 39, 256-8.

15.       Snider, B. B. “Lewis Acid Catalysis of Ene Reactions” J. Org. Chem. 1974, 39, 255-256.

14.        Snider, B. B. “New Method for the Preparation of 4-Methylene-1-cyclohexenes” J. Org. Chem. 1973, 38, 3961-3963.

13.        Corey, E. J.; Snider, B. B. “The Preparation of 1,3,4-Thiadiazoline-2,5-dione and its Use as a Dienophile” J. Org. Chem. 1973, 38, 3632-3633.

12.        Corey, E. J.; Snider, B. B. “New Synthetic Route to Prostaglandins” Tetrahedron Lett. 1973, 3091-4.

11.        Salamone, J. C.; Israel, S. C.; Taylor, P.; Snider, B. “Poly(vinylimidazolium) salts of varying Hydrophilic-Hydrophobic Character” J. Polym. Sci., Polym. Symp. 1974, 45, 65-73.

The homopolymerizations of a series of 3-n-alkyl-1-vinylimidazolium iodides are described in which the length of the quaternizing alkyl group was varied from methyl to n-propyl to n-hexyl to n-heptyl to n-dodecyl to n-hexadecyl. The preparations of these cationic monomers have previously been reported through reaction of 1-vinylimidazole with the corresponding n-alkyl iodide. All polymerizations were performed in aqueous solution at the same molar concentration of monomer using the free radical initiator 4,4′-azobis-4-cyanopentanoic acid. It was found that the short side-chain polyions (methyl and n-propyl) were water soluble, whereas the more hydrophobic intermediate side-chain polyions (n-hexyl and n-heptyl) were water insoluble. The long side-chain polyions (n-dodecyl and n-hexadecyl), on the other hand, being highly hydrophobic, appeared to form polysoaps and remained in aqueous solution. The solution behavior of these polyions in water, in aqueous salt solution, and in chloroform is discussed as well as is the critical micelle concentration of a long side-chain polyion and its corresponding monomer.

7.          Corey, E. J.; Snider, B. B. “Total Synthesis of (±)-Fumagillin” J. Am. Chem. Soc. 1972, 94, 2549-50.

5.          Salamone, J. C.; Snider, B.; Fitch, W. L. “Polymerization of 4-Vinylpyridinium salts. III. Clarification of the Mechanism of Spontaneous Polymerization” J. Polym. Sci. A-1 1971, 9, 1493-1504.

The mechanism of the spontaneous polymerization of 4-vinylpyiridine on quaternization or protonation has been investigated. Results indicate that initiation is caused by the nucleophilic attack of 4-vinylpyridine on the double bond of 4-vinylpyridinium ion. It was shown that halide ions do not contribute significantly to the initiation. In the case of acid salts of 4-vinylpyridine a hydrogen-transfer polymerization occurred to give an ionene polymer with pyridinium units in the main chain. The “matrix” polymerization of 4-vinylpyridine on poly(phosphoric acid) or poly(acrylic acid) also resulted in ionene formation. Conditions under which stable 4-vinylpyridinium salts can be obtained are discussed.

4.         Salamone, J. C.; Snider, B.; Fitch, W. L. “Polymerization of 4-Vinylpyridinium Salts. I. Counterion Initiation Mechanism” J. Polym. Sci. B 1971, 9, 13-17.

3.           Salamone, J. C.; Snider, B.; Fitch, W. L. “Polymerization of 4-Vinylpyridinium salts. II. Hydrogen-Transfer Polymerization” Macromolecules 1970, 3, 707-709.

1.          Salamone, J. C.; Snider, B. “Quaternary Ammonium Polymers from 1,4-Diaza[2.2.2]bicyclooctane” J. Polym. Sci. A-1 1970, 8, 3495-3501.

Menschutkin reactions of 1,4-diaza[2.2.2]bicyclooctane with various α,α-dibromoalkanes and α,α′-dibromoxylenes have been studied in two solvent systems and at different temperatures. It was found that quaternary ammonium polymers could easily be prepared from this rigid, bicyclic, ditertiary amine.