Modern instrumental techniques in the structure elucidation of products derived from petrochemicals

Butler, Peter Earle.; Mueller, W. H.; Reed, John J. R.

doi:10.1021/es60004a001

Cited by 4 publications

(1 citation statement)

References 14 publications

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“…I n solvents such as chlorinated hydrocarbons or ethyl acetate both alkyl-and aryl-substituted acetylenes afford mostly products of structure (57). However, in acetic acid the reaction of phenylacetylene with either 2,4-dinitrobenzenesulfenyl chloride r511 or methanesulfenyl chloride [501 produced predominantly the opposite adduct orientation (58).…”

Section: Unsaturated Thiiranium Ionsmentioning

confidence: 99%

Thiiranium Ions as Reaction Intermediates

Mueller

1969

Angew. Chem. Int. Ed. Engl.

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Conclusion and OutlookWithin certain limits the anhydride method has proved a simple and effective process for the preparation of substituted sesquifulvalenes and of the iso-z-electronic cyclopentadienylidenepyrans and -thiopyrans. Only a selection of the possible reactions has been described in this article. Preliminary experiments have shown that various other ketones that are iso-rc-electronic with tropone and contain more than one hetero atom also undergo condensation to heterosesquifulvalenes by the same synthetic route. Similarly, the benzotropone analogs furo [3,4-d] The addition of sulfenyl chlorides or suvur dichloride to unsaturated compounds proceeds via thiiranium ions. The present article reviews the electronic and steric factors influencing the nature oj these ions and their effects on subsequent ring opening and product formation. For the purpose of this discussion results primarily from electrophilic ring opening have been chosen to illustrate these factors. Solvent and temperature efects have been disregarded.

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Section: Unsaturated Thiiranium Ionsmentioning

confidence: 99%

Thiiranium Ions as Reaction Intermediates

Mueller

1969

Angew. Chem. Int. Ed. Engl.

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Thiiranium‐Ionen als Reaktionszwischenstufen

Mueller

1969

Angewandte Chemie

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Die Addition von Sulfenylchloriden oder von Schwefeldichlorid an ungestittkte Verbindungen verliuft uber Thiiranium-Ionen. In diesem Aufsatz werden die elektronischen und sterischen Faktoren besprochen, welche die Natur dieser Zonen sowie die anschliejende Ringoffnung und Produktbildung beeinflussen. Fur die Diskussion wurden in erster Linie durch elektrophile Agentien bewirkte Ringoffnungen ausgewahlt. Losungsmittel-undTemperatureffekte mujten vernachltissigt werden.

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