Zur Frage der Existenz von Sulfenen, II Abfangen von Sulfenen durch Cycloaddition an Keten‐<i>N.N</i>‐acetale

A. IntroductionSulfines are the S-oxides and sulfenes 121 the S,S-dioxides of thioaldehydes and thioketones. They are formally the inner anhydrides of sulfinic and sulfonic acids respectively, just as ketenes are inner anhydrides of carboxylic acids. S-oxides and S,S-dioxides of thiocarboxylic acid derivatives such as chlorides or amides are not regarded as sulfines or sulfenes.electrons of the S atom are involved in bonding. Sulfenes are derivatives of sulfur trioxide, and sulfines are derivatives of sulfur dioxide, one 0 atom in each case being replaced by an alkylidene group. Sulfines (like sulfinic acids and dialkyl sulfoxides) have a lone pair of electrons on the S atom, whereas in the sulfenes (as in sulfonic acids and dialkylsulfones), all the [2] T. J . Wa"ace, Quart. Rev. (chem. SOC., London) 20,67 (1966).[3] E. Wedekind and D. Schenk, Ber. dtsch. chem. Ges. 44, 198 (1911).[41 H.Stuudinger: Die Ketene. F. Enke,Stuttgart 1912,pp.92,129. [51 W. A . Sheppard and J. Diekmann, J. Amer. chem. SOC. 86, 1891 (1964). 161 In this paper sulfines and sulfenes are named generally as derivatives of sulfine (CHz=SO) and sulfene (CHz=SOz), by analogy with the ketenes, and occasionally as oxides or dioxides of thioaldehydes or thioketones. If the C atom of the CH2 group forms part of a ring, the groups =SO and =SO2 should be designated by the prefixes "sulfinyl" and "sulfonyl", respectively. Thus (5) is called 9-sulfinylfluorene. This suggestion is based on the rule for ketenes (=CO = carbonyl when the CH2 group forms part of a ring).

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Zur Frage der Existenz von Sulfenen, II Abfangen von Sulfenen durch Cycloaddition an Keten‐N.N‐acetale

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Four‐Membered Sulfur Heterocycles

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