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Journal articles on the topic 'Episulfonium ion'

Author: Grafiati
Published: 4 June 2021
Last updated: 10 February 2022

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1

Kosugi, Hiroshi, Hiroshi Tanaka, Issei Tsukamoto, and Michiharu Kato. "Asymmetric Polyene Cyclization Via Episulfonium Ion." Phosphorus, Sulfur, and Silicon and the Related Elements 153, no. 1 (1999): 311–12. http://dx.doi.org/10.1080/10426509908546446.

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2

Fox, David J., Thomas J. Morley, and Stuart Warren. "Episulfonium ion-mediated cyclic peptide and triazine synthesis." Organic & Biomolecular Chemistry 4, no. 16 (2006): 3120. http://dx.doi.org/10.1039/b606882k.

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3

Kim, Sunggak, and Jung Ho Park. "An episulfonium ion mediated ring expansion of 1-alkenylcycloakanols." Tetrahedron Letters 30, no. 45 (1989): 6181–84. http://dx.doi.org/10.1016/s0040-4039(01)93336-2.

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4

Henkel, James G., and George S. Amato. "Methyl mercapturate episulfonium ion: a model reactive metabolite of dihaloethanes." Journal of Medicinal Chemistry 31, no. 7 (1988): 1279–82. http://dx.doi.org/10.1021/jm00402a003.

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5

Edstrom, Eric D., and Tom Livinghouse. "Formation of episulfonium ions from alkenes. Application to the synthesis of higher order carbocycles via episulfonium ion initiated polyene cyclizations." Journal of Organic Chemistry 52, no. 5 (1987): 949–51. http://dx.doi.org/10.1021/jo00381a049.

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6

Tuladhar, Sudersan M., and Alex G. Fallis. "Cyclic ether synthesis: sulfenyletherification with benzenesulfenyl chloride/N, N-diisopropylethylamine and sulfenate ester cycloadditions." Canadian Journal of Chemistry 65, no. 8 (1987): 1833–37. http://dx.doi.org/10.1139/v87-308.

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A general method for the formation of the cyclic ethers 9, 10, 13, 14, 16, and 28 and the lactone 30 is described. The procedure employs benzenesulfenyl chloride prepared insitu in acetonitrile and N,N-diisopropylethylamine to generate a thiiranium (episulfonium) ion intermediate from which the cyclic products arise by internal nucleophilic displacement. In the special case of the norbornene alcohols 1 and 2 the oxetanes 5 and 6 are formed by intramolecular sulfenate ester cycloaddition.
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7

Branchaud, Bruce P., and Heather S. Blanchette. "Highly stereoselective Friedel–Crafts alkylations of unactivated benzenes by episulfonium ion cyclizations." Tetrahedron Letters 43, no. 3 (2002): 351–53. http://dx.doi.org/10.1016/s0040-4039(01)02173-6.

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8

Huang, Sheng-Xiong, Bong-Sik Yun, Ming Ma, et al. "Leinamycin E1 acting as an anticancer prodrug activated by reactive oxygen species." Proceedings of the National Academy of Sciences 112, no. 27 (2015): 8278–83. http://dx.doi.org/10.1073/pnas.1506761112.

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Leinamycin (LNM) is a potent antitumor antibiotic produced by Streptomyces atroolivaceus S-140, featuring an unusual 1,3-dioxo-1,2-dithiolane moiety that is spiro-fused to a thiazole-containing 18-membered lactam ring. Upon reductive activation in the presence of cellular thiols, LNM exerts its antitumor activity by an episulfonium ion-mediated DNA alkylation. Previously, we have cloned the lnm gene cluster from S. atroolivaceus S-140 and characterized the biosynthetic machinery responsible for the 18-membered lactam backbone and the alkyl branch at C3 of LNM. We now report the isolation and c
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9

King, James Frederick, and Kishan Chand Khemani. "Synthesis and thermolysis of 2-(phenylthio)ethanesulfonyl chloride. The absence of a reported "rearrangement of radicals with migration of the chlorine atom from sulfur to carbon"." Canadian Journal of Chemistry 63, no. 3 (1985): 619–22. http://dx.doi.org/10.1139/v85-101.

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2-(Phenylthio)ethanesulfonyl chloride (1) is the major product of the reaction of (a) lithium 2-(phenylthio)ethanesulfinate (6) and chlorine, and, notwithstanding contrary reports, also of (b) benzenethiol (3) and ethenesulfonyl chloride (4), and (c) sodium 2-(phenylthio)ethanesulfonate (5) and phosphorus pentachloride. The rearrangement referred to in the title, which was proposed to account for the isolation of 2-(phenylthio)ethyl chloride (2) rather than 1 from 3 and 4, therefore does not occur. Desulfonylation of 1 to form 2, however, readily takes place thermally and, in accord with a rat
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10

TOSHIMITSU, A., C. HIROSAWA, and S. TANIMOTO. "ChemInform Abstract: Enantioselectivity in the Ritter-Type Substitution Reaction via Episulfonium Ion: Retention of Configuration." ChemInform 23, no. 20 (2010): no. http://dx.doi.org/10.1002/chin.199220133.

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11

Faustov, V. I., and W. A. Smit. "Quantum chemical study of reactions of episulfonium ions. 1. Comparative MNDO study of opening of the episulfonium ion ring by neutral nucleophiles and SN2 substitution in protonated methylthiol." Bulletin of the Academy of Sciences of the USSR Division of Chemical Science 38, no. 7 (1989): 1439–45. http://dx.doi.org/10.1007/bf00978435.

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12

Pearson, Paul G., Erik J. Soderlund, Erik Dybing, and Sidney D. Nelson. "Metabolic activation of 1,2-dibromo-3-chloropropane: evidence for the formation of reactive episulfonium ion intermediates." Biochemistry 29, no. 20 (1990): 4971–81. http://dx.doi.org/10.1021/bi00472a030.

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13

Johnston, Blair D., and B. Mario Pinto. "Synthesis of Thio-Linked Disaccharides by 1→2 Intramolecular Thioglycosyl Migration: Oxacarbenium versus Episulfonium Ion Intermediates." Journal of Organic Chemistry 65, no. 15 (2000): 4607–17. http://dx.doi.org/10.1021/jo000226k.

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14

LOPEZ-TUDANCA, P. L., K. JONES, and P. BROWNBRIDGE. "ChemInform Abstract: Substituent Control in the Synthesis of Tetrahydropyrans, Oxepanes and Oxocanes by Episulfonium Ion-Mediated Cyclization." ChemInform 23, no. 10 (2010): no. http://dx.doi.org/10.1002/chin.199210083.

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15

Webb, William W., Adnan A. Elfarra, Kathy D. Webster, Rebecca E. Thom, and M. W. Anders. "Role for an episulfonium ion in S-(2-chloroethyl)-DL-cysteine-induced cytotoxicity and its reaction with glutathione." Biochemistry 26, no. 11 (1987): 3017–23. http://dx.doi.org/10.1021/bi00385a010.

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16

Peterson, Lisa A., Thomas M. Harris, and F. Peter Guengerich. "Evidence for an episulfonium ion intermediate in the formation of S-[2-(N7-guanyl)ethyl]glutathione in DNA." Journal of the American Chemical Society 110, no. 10 (1988): 3284–91. http://dx.doi.org/10.1021/ja00218a045.

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17

Johnston, Blair D., and B. Mario Pinto. "ChemInform Abstract: Synthesis of Thio-Linked Disaccharides by 1→2 Intramolecular Thioglycosyl Migration: Oxacarbenium versus Episulfonium Ion Intermediates." ChemInform 31, no. 47 (2000): no. http://dx.doi.org/10.1002/chin.200047188.

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18

Edstrom, Eric, and Tom Livinghouse. "New methods for the generation of episulfonium ions. An application to the synthesis of carbocycles via sulfenium ion promoted arene-alkene cyclizations." Journal of the American Chemical Society 108, no. 6 (1986): 1334–36. http://dx.doi.org/10.1021/ja00266a055.

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19

Kaetzel, Rhonda S., Martha D. Stapels, Douglas F. Barofsky, and Donald J. Reed. "Alkylation of protein disulfide isomerase by the episulfonium ion derived from the glutathione conjugate of 1,2-dichloroethane and mass spectrometric characterization of the adducts." Archives of Biochemistry and Biophysics 423, no. 1 (2004): 136–47. http://dx.doi.org/10.1016/j.abb.2003.10.016.

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20

Ma, Ming, Jeremy R. Lohman, Tao Liu, and Ben Shen. "C-S bond cleavage by a polyketide synthase domain." Proceedings of the National Academy of Sciences 112, no. 33 (2015): 10359–64. http://dx.doi.org/10.1073/pnas.1508437112.

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Leinamycin (LNM) is a sulfur-containing antitumor antibiotic featuring an unusual 1,3-dioxo-1,2-dithiolane moiety that is spiro-fused to a thiazole-containing 18-membered lactam ring. The 1,3-dioxo-1,2-dithiolane moiety is essential for LNM’s antitumor activity, by virtue of its ability to generate an episulfonium ion intermediate capable of alkylating DNA. We have previously cloned and sequenced the lnm gene cluster from Streptomyces atroolivaceus S-140. In vivo and in vitro characterizations of the LNM biosynthetic machinery have since established that: (i) the 18-membered macrolactam backbo
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21

KIM, S., and J. H. PARK. "ChemInform Abstract: An Episulfonium Ion Mediated Ring Expansion of 1-Alkenylcycloalkanols." ChemInform 21, no. 23 (1990). http://dx.doi.org/10.1002/chin.199023164.

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22

EDSTROM, E. D., and T. LIVINGHOUSE. "ChemInform Abstract: On the Direct Formation of Episulfonium Ions from Alkenes. An Application to the Synthesis of Higher Order Carbocycles via Episulfonium Ion Initiated Polyene Cyclizations." ChemInform 18, no. 41 (1987). http://dx.doi.org/10.1002/chin.198741115.

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23

Vektarienė, Aušra, and Gytis Vektaris. "A theoretical study of styrene and sulfenyl chloride reaction mechanism." Chemija 29, no. 3 (2018). http://dx.doi.org/10.6001/chemija.v29i3.3819.

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The classical description of sulfenyl halides additions to olefins proposes the formation of an episulfonium ion intermediate during the reaction path. However, a careful analysis of experiments performed in the past suggests that there should not be a single mechanistic picture of sulfenyl halide additions to substituted olefins. Our work is the first theoretical study of detailed insights into the mechanism of methylsulfenchloride addition to styrene. The reaction potential energy profile has been calculated by means of the B3LYP functional with the 6-31++G(d, p) basis set. Mixing of the mol
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24

PETERSON, L. A., T. M. HARRIS, and F. P. GUENGERICH. "ChemInform Abstract: Evidence for an Episulfonium Ion Intermediate in the Formation of S-(2-(N7-Guanyl)ethyl)glutathione in DNA." ChemInform 19, no. 36 (1988). http://dx.doi.org/10.1002/chin.198836351.

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25

EDSTROM, E. D., and T. LIVINGHOUSE. "ChemInform Abstract: New Methods for the Generation of Episulfonium Ions. An Application to the Synthesis of Carbocycles via Sulfenium Ion Promoted Arene-Alkene Cyclizations." Chemischer Informationsdienst 17, no. 29 (1986). http://dx.doi.org/10.1002/chin.198629160.

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