CAS: 5905-47-5; Methyl1-Propenyldisulfide

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233666-09-6 15805-34-2 5905-46-4

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methanethiosulfonic acid S-methyl ester n-propyl trans-1-propenyl sulfide

📜甲基硫代磺酸甲酯,N-Propyl Trans-1-Propenyl Sulfide置于氨,Lithium体系中,化学反应生成 甲基丙-1-烯基二硫醚
参考文献:Allium Chemistry: Synthesis And Sigmatropic Rearrangements Of Alk(En)Yl 1-Propenyl Disulfide S-Oxides From Cut Onion And Garlic1
标题:Allium Chemistry: Synthesis And Sigmatropic Rearrangements Of Alk(En)Yl 1-Propenyl Disulfide S-Oxides From Cut Onion And Garlic1
摘要:Reduction (Lialh4) Of Propyl 1-Propynyl Sulfide (8) To (E)-1-Propenyl Propyl Sulfide ((E)-10),C-S Cleavage (Li/nh3) To Lithium (E)-1-Propenethiolate (Li(E)-11),And Reaction With Meso(2)Cl Gives (E,E)-Bis(1-Propenyl) Disulfide ((E,E)-2); I-Bu(2)Alh Reduction Of 8 To (Z)-10 And Reaction With Li/nh3 And Then Meso(2)Cl Gives (Z,Z)-2 Via Li (Z)-11. Reaction Of Meso(2)Sr (R = Me (12A),N-Pr (12B),Ch2Ch=ch2 (12C),Ch=chme (12D)) With K (E)-11 Gives (E,Z)-2 From (Z)-12D; Li (E,Z)-11 Gives Alkyl (E)-And (Z)-1-Propenyl Disulfides (Mech=chssr,R = Me (3A),N-Pr (3B),Ch2=chch2 (3C)) From 12A-C,Respectively. Oxidation At-60 Degrees C Of (E,E)-,(Z,Z)-,And (E,Z)-2 Gives (E)-1-Propenesulfinothioic Acid S-(E)-1-Propenyl Ester ((E,E)-13,(E,E)-Mech=chs(O)Sch=chme) From (E,E)-2,(Z,Z)-13 From (Z,Z)-2,And Ca. 2:1 (E,Z)-13)/(Z,E)-13 From (E,Z)-2. Warming (Z,Z)-13 Gives (+/-)-(1 Alpha,2 Alpha,3 Beta,4 Alpha,5 Beta)-2,3-Dimethyl-5,6-Dithiabicyclo[2.1.1]Hexane 5-Oxide (1A),Endo-5-Methyl-Exo-6-Methyl-2-Oxa-3,7-Dithiabicyclo[2.2.1]Heptane (14A),And Exo-5-Methyl-Endo-6-Methyl-2-Oxa-3,7-Dithiabicyclo[2.2. 1]Heptane (14B). Warming (E,E)-13 Gives 14A And 14B; (E,Z)-13/(Z,E)-13 Gives (1 Alpha,2 Alpha,3 Alpha,4 Alpha,5 Beta)-2,3-Dimethyl-5,6-Dithiabicyclo[2.1.1]Hexane 5-Oxide (1B),Exo-5-Methyl-Exo-6-Methyl-2-Oxa-3,7-Dithiabicyclo[2.2.1]Heptane (14C),And Endo-5-Methyl-Endo-6-Methyl-2-Oxa-3,7-Dithiabicyclo[2.2.1]Heptane (14D). Oxidation Of 3A-C Gives Mech=chss(O)R (4) And Mech=chs(O)Sr (5). At-60 Degrees C,M-Cpba (2 Equiv) Converts (E,E)-2 Into (Z,Z)-D,L-2,3-Dimethyl-1,4-Butanedithial 1,4-Dioxide (26) While (Z,Z)-2 Gives Meso-And D,L-26. With Naio4,4/5 (R = Me) Gives (E)-Or (Z)-12A And Mech=chso(2)Sme (6A); With M-Cpba (Z)-Mes(O)Chmech=s+-O-(25A) Forms. At 85 Degrees C 2 Gives 1:1 Cis-And Trans-2-Mercapto-3,4-Dimethyl-2,3-Dihydrothiophene (29).
DOI:10.1021/ja953444H