Polymethylation reactions of saturated and unsaturated thiacrown ethers

Hirabayashi, Kazunori; Sugano, Nanami; Nakashizuka, Masahito; Yaginuma, Tatsuya; Shimizu, Toshio

doi:10.1080/10426507.2019.1603722

Cited by 2 publications

(5 citation statements)

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“…In the case of 5 b, colorless needles were precipitated by using acetone/diethyl ether. [8] These compounds were characterized by single-crystal X-ray diffraction analysis. The formation of sulfonium groups was confirmed from the X-ray crystal structures (Figure 1).…”

Section: Resultsmentioning

confidence: 99%

“…Mono‐ and dimethylated products 5 a and 5 b ( cis adduct) were also prepared by the reactions of unsaturated thiacrown ether 4 and 2 (Scheme 3). [8] The yield of 5 b was improved to 57% by using 4 mmol of 2 .…”

Section: Resultsmentioning

confidence: 99%

“…Single crystals of 3 a and 3 b were prepared by recrystallization from acetonitrile/diethyl ether. In the case of 5 b , colorless needles were precipitated by using acetone/diethyl ether [8] . These compounds were characterized by single‐crystal X‐ray diffraction analysis.…”

Section: Resultsmentioning

confidence: 99%

“…[6] In addition, we investigated the transformation of the unsaturated thiacrown ethers by oxidation, [7] as well as the polymethylation of 12-membered saturated and 15-membered unsaturated thiacrown ethers. [8] In this paper, we report the synthesis of 18-membered unsaturated thiacrown ethers possessing sulfonium groups by the alkylation reaction of the 18-membered unsaturated thiacrown ethers. We also discuss some properties of 15-and 18membered unsaturated thiacrown ethers possessing sulfonium groups.…”

Section: Introductionmentioning

confidence: 99%

“…Previously, we reported the synthesis and properties of unsaturated thiacrown ethers, and the formation of transition metal complexes [6] . In addition, we investigated the transformation of the unsaturated thiacrown ethers by oxidation, [7] as well as the polymethylation of 12‐membered saturated and 15‐membered unsaturated thiacrown ethers [8] . In this paper, we report the synthesis of 18‐membered unsaturated thiacrown ethers possessing sulfonium groups by the alkylation reaction of the 18‐membered unsaturated thiacrown ethers.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, Structure, and Properties of Unsaturated Thiacrown Ethers Possessing Sulfonium Groups

Hirabayashi

Nakashizuka

Shimizu

2022

Chemistry An Asian Journal

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Thiacrown ethers have attracted much attention in host-guest chemistry. Herein, we present the polymethylation reactions of unsaturated thiacrown ethers. Unsaturated thiacrown ethers having sulfonium groups were synthesized by the reaction of corresponding unsaturated thiacrown ethers with methyl triflate. The obtained methylated unsaturated thiacrown ethers were characterized by single-crystal Xray diffraction analysis, UV absorption measurement, and cyclic voltammetry. The occupied and unoccupied molecular orbitals of the obtained methylated unsaturated thiacrown ethers are essentially localized respectively around the sulfide groups and the sulfonium groups. Furthermore, the results of electrostatic potential maps indicated that positive charges were distributed throughout the entire unsaturated thiacrown ether moieties.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations