ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Syntheses of 3-Hydroxy-4-methyl-3-cyclobutene-1,2-dione (Methylmoniliformin)New routes to 3-hydroxy-4-methyl-3-cyclobutene-1,2-dione (9), the lowest homologue of the mycotoxine moniliformin are described. A common feature of all pathways is the synthesis of methylcyclobutanes having the oxidation level 6. Precursors, which are easily transformed to 9 by acid catalyzed hydrolysis, include [2+2]-cycloadducts of in situ generated methyl ketene to tetraethoxyethylene and [2+2]-photocycloadducts of dichlorovinylenecarbonate with 1,1-dichloro-1-propene. The acid hydrolysis of [2+2]-cycloadducts of chlorotrifluoroethylene to N, N-diethyl-1-propynylamine yields the diethylamide of 9 (=22) in 50% overall yield. In addition, a convenient one-pot-two-steps synthesis of a new electronrich ethylene, 1,1,2-triethoxy-2-trimethylsilyloxy-ethylene (11), is described.
Additional Material:
2 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19800630504
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