Journal of Organic Chemistry p. 5624 - 5627 (1993)
Update date:2022-08-03
Topics:
Edema, Jilles J. H.
Buter, Jan
Schoonbeek, Franck S.
Meetsma, Auke
Bolhuis, Fre van
Kellogg, Richard M.
Cyclization of the bis cesium thiolate (generated in situ) of 1,3-dimercaptoacetone (1) with α,ω-dihalides in DMF affords the corresponding cyclic thioethers in good yields, providing an efficient alternative route to keto-functionalized thio-crown ethers.A previously suggested dimeric structure for 1 is supported by NMR spectra, which also allow distinction between cis and trans isomers of 1.Equilibration between the isomers can also be followed by NMR.The molecular structures of two specific thio-crown ethers have been determined by X-ray crystallography.Crystal data for 2,5,9,12-tetrathia-7-oxo-(13)-m-benzophane (8) at 130 K: triclinic, space group P-1; a = 7.230(1) Angstroem, b = 8.690(1) Angstroem, c = 13.253(1) Angstroem, α = 83.153(7) deg, β = 84.257(6) deg, γ = 85.575(6) deg, Z = 2, μ(Mo Kα) = 5.5 cm-1, R = 0.029 (Rw = 0.041) for 3082 reflections (I >/= 2.5?(I)).Crystal data for 1,4,7,10,13-pentathiacyclohexadecan-15-one (9) at 140 K: monoclinic space group P21/a; a = 16.558(1) Angstroem, b = 5.399(1) Angstroem, c = 16.734(1) Angstroem, β = 90.28(5) deg, Z = 4, μ(Mo Kα) = 7.3 cm-1, R = 0.048 (Rw = 0.66) for 3021 reflections (I >/= 3?(I)).
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Doi:10.1080/00397919308011185
(1993)Doi:10.1002/hlca.19930760210
(1993)Doi:10.1016/S0968-0896(99)00312-0
(2000)Doi:10.1021/jm049360d
(2004)Doi:10.1021/jm950558v
(1996)Doi:10.1016/S0040-4039(00)77654-4
(1993)