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Synthesen von 3‐Hydroxy‐4‐methyl‐3‐cyclobuten‐1,2‐dion (Methylmoniliformin)
Author(s) -
Bellus Daniel,
Martin Pierre,
Sauter Hanspeter,
Winkler Tammo
Publication year - 1980
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19800630504
Subject(s) - chemistry , cyclobutene , ketene , hydrolysis , yield (engineering) , propene , ethylene , medicinal chemistry , dehydrogenation , acid hydrolysis , organic chemistry , catalysis , ring (chemistry) , materials science , metallurgy
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.