三員環ジスルフィド,ジチイランの合成とその性質

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概要

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• The first isolable, unoxidized dithiirane, 3-phenyl-3- (1, 1, 3, 3-tetramethyl-4-oxo-4-phenylbutyl) dithiirane (16) was prepared by treatment of 2, 2, 4, 4-tetramethyl-1, 5-diphenyl-6, 7-dithiabicyclo- [3.1.1] heptane (14) with 2 KHSO<SUB>5</SUB>·KHSO<SUB>4</SUB>·K<SUB>2</SUB>SO<SUB>4</SUB> (OXONE<SUP>®</SUP>) or NaOCl-NaClO<SUB>4</SUB>. Monooxides of 14 gave the corresponding dithiirane 1-oxides 17 and 18 by reaction with OXONE<SUP>®</SUP>. Under similar conditions, some other dithiirane derivatives were obtained from 5, 6-dithiabicyclo [2.1.1] hexanes, 6, 7-dithiabicyclo [3. 1. 1] heptanes, and 7, 8-dithiabicyclo [4. 1. 1] octanes.<BR>It was disclosed by a study on competitive thermal reactions that a 3, 3-di-<I>tert</I>-alkyldithiirane is thermodynamically less stable but kinetically more stable than 3-alkyl-3-aryldithiirane 16.<BR>(1RS, 3SR) - and (1<I>RS</I>, 3<I>RS</I>) -Dithiirane 1-oxides, 17 and 18, respectively, were optically resolved by HPLC equipped with a chiral column and absolute configurations of the four stereoisomers were determined by X-ray single-crystal structure analysis and a chemical property. The mechanism of the racemization (1, 2-oxygen migration) between the respective enantiomers were also discussed.

• 社団法人 有機合成化学協会の論文
• 1997-10-01

著者

• 石井 昭彦

  埼玉大学理学部基礎化学科

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• 三員環ジスルフィド,ジチイランの合成とその性質

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