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|Section2= |Section3= }} In chemistry, 3,3,4,4-tetramethyltetrahydrofuran-2,5-dione is a heterocyclic compound with the formula , or (CH3)2(COC2COO)(CH3)2. It is a white crystalline solid with a pungent camphoraceous odor.〔 The compound is also called 3,3,4,4-tetramethyloxolane-2,5-dione (its IUPAC name) or 3,3,4,4-tetramethylsuccinic anhydride,〔 namely the anhydride of 2,2,3,3-tetramethylsuccinic acid, and sometimes abbreviated as TMSA.〔Subat Turdi, Peisheng Xu, Qun Li, Youqing Shen, Parhat Kerram, and Jun Ren (2008), ''Amidization of Doxorubicin Alleviates Doxorubicin-Induced Contractile Dysfunction and Reduced Survival in Murine Cardiomyocytes''. Toxicology Letters volume 178, issue 3, pages 197–201. 〕 It can be seen as derivative of tetrahydrofuran-2,5-dione (oxolane-2,5-dione) with two methyl groups replacing two hydrogen atoms on each of the carbon atoms in the ring that are not adjacent to the ring oxygen. 〔 "3,3,4,4-tetramethyloxolane-2,5-dione" at Molbase. Accessed on 2015-08-01.〕 ==Synthesis and chemistry== The compound is soluble in petrol ether. 〔〔 The compound was described in 1890 by Karl von Auwers and Victor Meyer who obtained it by thermal decomposition of 2,2,3,3-tetramethylsuccinic acid.〔Karl von Auwers, Victor Meyer (1890), ''Ueber Tetramethylbernsteinsäure und Trimethylglutarsäure.'' Berichte der deutschen chemischen Gesellschaft, volume 23, issue 1, pages 293,301,304–305. 〕〔Karl von Auwers, O. Ungemach (1935) ''Zur Zerreißbarkeit der Kohlenstoffkette in Bernsteinsäure-Derivaten.'' Berichte der deutschen chemischen Gesellschaft, volume 68, pages 23, 349–351. 〕 It can also be obtained, in > 50% yield, from 3,3,4,4-tetramethylpyrrolidine-2,5-dione 〔Snezna Bizilj, David P. Kelly, Algirdas K. Serelis, David H. Solomon, Kathleen E. White (1985). ''The Self-Reactions of 1-Methoxycarbonyl-1-methylethyl and Higher Ester Radicals: Combination vs Disproportionation and Oligomeric Products from Secondary Reactions.'' Australian Journal of Chemistry, volume 38, issue 11, pages 1657–1673. 〕 Other synthesis routes include * treatment of 2,2'-Azobis(2-methylpropionitrile) with sulfuric acid (1896) 〔J. Thiele, K. Heuser (1896). ''Ueber Hydrazinderivate der Isobuttersäure.'' Justus Liebigs Annalen der Chemie, volume 290, pages 1–43.〕 * decomposition of the hydroxy-lactone of 2,2,3,3-tetramethyl-1-one-glutaric acid with release of carbon monoxide (1927) 〔Eugene Rothstein, Charles William Shoppee (1927), ''Ring-chain tautomerism. Part XV. The hydroxy-lactone type.'' Journal of the Chemical Society (UK; Resumed), article LXXVIII, pages 531-534. .〕 抄文引用元・出典: フリー百科事典『 ウィキペディア（Wikipedia）』 ■ウィキペディアで「3,3,4,4-Tetramethyltetrahydrofuran-2,5-dione」の詳細全文を読む スポンサード リンク
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