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  • 1
    ISSN: 0170-2041
    Keywords: Thiophenes ; 3,7-Dioxabicyclo[3.3.0]octanes ; Aldol additions ; Lactones ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Reactions of Trialkylsilyl Trifluoromethanesulfonates, XII.  -  Aldol-Type Reactions with 2,6-Bis(trimethylsiloxy)thiophene Synthesis of Bicyclic γ-LactonesIn the presence of trimethylsilyl triflate (2) aromatic aldehydes 4 react with 2,6-bis(trimethylsiloxy)thiophene (3) to yield the 3,4-disubstituted thiosuccinic anhydrides 5. By hydrolysis of the products 5 in the presence of lead acetate the diaryl-substituted cis-bislactones 8 are obtained. Dialkyl-substituted cis-bislactones 10 are formed in a aldol addition of aliphatic aldehydes 9 to 3 catalysed by zinc chloride and subsequent hydrolysis of the intermediates. The synthesis of 3,4-bis(dialkoxyalkyl)thiosuccinic anhydrides 7 is achieved by the reaction of 3 with carboxylic acid orthoesters 6 catalysed by 2.
    Additional Material: 11 Tab.
    Type of Medium: Electronic Resource
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