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
URL:
http://dx.doi.org/10.1002/jlac.1992199201105
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