ISSN:
0009-2940
Keywords:
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Description / Table of Contents:
Synthesis of 2.-3(Carboxymethylene)- and 2.-3(2-Hydroxyethylidene)-2.3-dideoxy-D-mannose - Monosaccharides with a Cyclopropane RingThe anhydro derivative 1 yielded the cyclopropane carboxylic ester 2 in a PO-activated olefination reaction. Under mild conditions 2 could be hydrolised to the free carboxylic acid 5. By reduction the cyclopropyl carbinol 13 and the cyclopropane carbaldehyde 21 were formed. The latter could be rearranged to the cyclobutene derivative 25. Attempts to synthesize a cyclopropanol were unsuccessful.
Notes:
Durch PO-aktivierte Olefinierung entstand aus der Anhydro-Verbindung 1 der Cyclopropancarbonsäureester 2, der unter milden Bedingungen zur freien Carbonsäure 5 hydrolysiert werden konnte. Reduktion lieferte das Cyclopropylcarbinol 13 und den Cyclopropan-carbaldehyd 21, der zum Cyclobutenderivat 25 umgelagert wurde. Die Synthese eines Cyclopropanols gelang nicht.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19721050233
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