The Preparation and Properties of Methylene Di-n-butyl Disulfone

Stutz, Robert E.; Shriner, R. L.

doi:10.1021/ja01330a066

Cited by 23 publications

(1 citation statement)

References 3 publications

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“…When a neutral MeOH solution of the enone 7 and n-BuSH was stirred at 25°without an added radical initiator, none of either ketone 40 or 41 was detected. A collected (glpc) sample of the ketone 40 was obtained as a colorless liquid: n25o 1.4648; ir (CCU) 1710 cm-1 (0=0); nmr (CCU), 2.3-3.1 (5 H, m, CH2CO, CH2SCH) and 0.8-1.7 [(25 H, m, aliphatic CH including two 9 H singlets at 0.98 and 1.13 (t-Bu)]; mass spectrum m/e (rel intensity) 258 (M+, <1), 111 (32), 95 (45), 58 (100), 57 (78), 43 (65), and 41 (26).…”

Section: Experimental Section21mentioning

confidence: 99%

Reactions involving electron transfer. IV. Reduction of enones with chromium(II) compounds

House¹,

Kinloch²

1974

J. Org. Chem.

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Solutions of the Cr(II) complex, Cr(en)2(0Ac)2, in MeOH are capable of reducing simple ,/3-unsaturated ketones to the corresponding saturated ketones. With 2-cyclohexenone derivatives 10 and 11 that contain a 3-alkyl substituent, preparatively useful yields of the reduced products may be obtained provided a proton donor (HOAc) and a good hydrogen atom donor (re-PrSH or rc-BuSH) are also present in the reaction mixture. With enones 7, 12, and 13 that have only one /3-alkyl substituent, the presence of the above additives still does not afford high yields of saturated ketones because of a competing addition of the mercaptan to the enone system. Various types of evidence are offered to support the proposal that these reductions proceed by successive reactions of the enone with 2 equiv of the Cr(II) complex to form the intermediates illustrated in Scheme III.Solutions containing salts of the chromium(II) ion, either aquated or coordinated with various nitrogen ligands such as ammonia or ethylenediamine, have been used for the reduction of various organic compounds2 including alkyl and aryl halides,36•4 certain ,/3-unsaturated carbonyl compounds3®•5 certain acetylenes,6 and various unsaturated nitrogen compounds such as oxime acetates,7® azides,76 and nitro compounds.70 In connection with our earlier studies of reductions of ,/3-unsaturated carbonyl compounds by processes involving successive electron transfers,8 we wished to examine various Cr(II) derivatives as potential agents for effecting reductions of this type. Previous studies5®•0•6•6®•6 had indicated that doubly activated multiple C-C bonds such as that present in compounds of the type RCOCH=CHCOR or RCOC=CCOR could be reduced with solutions of CrCl2 or CrSCL in water or aqueous dimethylformamide (DMF). With this reducing agent, Cr(H20)e2+, less easily reduced conjugated carbonyl compounds (e.g., RCH=CHCOR) were either recovered unchanged or converted to dihydro dimers RCOCH2CH(R)CH(R)CH2COR,5® Studies with solutions A New Ring Expansion Procedure. VI. The Decomposition of the Magnesium Salts of Some l-(a-Bromobenzyl)-l-cycloalkanols and Bicycloalkanols

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Section: Experimental Section21mentioning

confidence: 99%

Reactions involving electron transfer. IV. Reduction of enones with chromium(II) compounds

House¹,

Kinloch²

1974

J. Org. Chem.

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Über Reaktionen mit Aluminiumalkylen, VI. Zur Reaktion von Triäthylaluminium und Äthylaluminiumsesquichlorid mit Sulfonsäurechloriden

Reinheckel

Jahnke

1966

Chem. Ber.

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Chalkogenolat‐Ionen und ihre Derivate, IV. Darstellung und Eigenschaften von Tellur(IV)‐thiolaten und ‐dithiolaten

Nakhdjavan

Klar

1977

Justus Liebigs Ann. Chem.

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Tellur(IV)‐thiolate 9 und ‐dithiolate 10 können durch Umsetzung von Tellur(IV)‐chlorid mit den erforderlichen Molmengen Thiolen bzw. Dithiolen in Ethanol als Lösungsmittel bei tiefen Temperaturen als gelbe bis braune, kristalline Produkte erhalten werden. Die Verbindungen zersetzen sich thermisch zu Tellur und den entsprechenden Disulfiden. Mit 10 als Ausgangssubstanz läßt sich diese Reaktion zu einer gezielten Synthese der sonst nur schwer zugänglichen cyclischen Bis(disulfide) 3 ausnutzen.

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The Preparation and Properties of Methylene Di-n-butyl Disulfone

Cited by 23 publications

References 3 publications

Reactions involving electron transfer. IV. Reduction of enones with chromium(II) compounds

Reactions involving electron transfer. IV. Reduction of enones with chromium(II) compounds

Über Reaktionen mit Aluminiumalkylen, VI. Zur Reaktion von Triäthylaluminium und Äthylaluminiumsesquichlorid mit Sulfonsäurechloriden

Chalkogenolat‐Ionen und ihre Derivate, IV. Darstellung und Eigenschaften von Tellur(IV)‐thiolaten und ‐dithiolaten

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