- Synthesis and chemistry of thiagermiranes
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Dimethylgermylene (1) reacts with thioketones 3 and 9 to give 1,3,2,4-dithiadigermolanes 4 and 10, the ultimate products of formation of thiagermiranes 6 and 11 and subsequent addition of dimethylgermanethione (7). Dimesitylgermylene (16) reacts with adamantanethione (3) to give 3-(2-adamantyl)-2,2-dimesityl-1,2-thiagermirane (18). Photolysis of thiagermirane 18 yields dimesitylgermylene (16) and adamantanethione (3) derived from germathiocarbonyl ylide 22. Oxidation of thiagermirane 18 by mCPBA gives 3-(2-adamantyl)-4,4-dimesityl-1,2,4-oxathiagermetane S-oxide (27). X-ray analyses were done for thiagermirane 18 and 1,2,4-oxathiagermetane S-oxide 27.
- Tsumuraya, Takeshi,Sato, Sadao,Ando, Wataru
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p. 161 - 167
(2008/10/08)
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- Thermal Cycloaddition Reactions of Thiocarbonyl Compounds. Part 2. 1,3-Dipolar Cycloaddition Reactions of Adamantanethione with Nitrile Oxides, Nitrilimines, and Diazoalkanes
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1,3-Dipolar cycloaddition of adamantanethione (1) with nitrile oxides, nitrilimines, and diazoalkanes occurred smoothly to afford regioselective cycloadducts, adamantane-2-spiro-5'-(1',4',2'-oxathiazolines) (4a-f), adamantane-2-spiro-2'-(1',3',4'-thiadiazolines) (11a-d), and (21b), respectively in high yields.These results are discussed on the basis of FMO and steric effects.
- Katada, Tomonori,Eguchi, Shoji,Sasaki, Tadashi
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p. 2641 - 2647
(2007/10/02)
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- Thermal Cycloaddition Reactions of Thiocarbonyl Compounds. Part 1. A Novel Cycloaddition Reaction of Adamantanethione with α,β-Unsaturated Carbonyl Compounds
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The thermal cycloaddition reaction of adamantanethione (1) with α,β-unsaturated carbonyl compounds such as acrolein, methacrolein, and methyl vinyl ketone occurred smoothly at 80 - 140 deg C to afford, regioselectively, adamantane-2-spiro-2'-(1'-oxa-3'-thiacyclohex-5'-enes) (3a-e) as novel cycloadducts in good yield.The nature of this cycloaddition is discussed on the basis of kinetics, solvent effects, and FMO theory.
- Katada, Tomonori,Eguchi, Shoji,Esaki, Toshiyuki,Sasaki, Tadashi
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p. 1869 - 1874
(2007/10/02)
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