𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Synthesen von 3-Hydroxy-4-methyl-3-cyclobuten-1,2-dion (Methylmoniliformin)

✍ Scribed by Daniel Bellus; Pierre Martin; Hanspeter Sauter; Tammo Winkler

Publisher
John Wiley and Sons
Year
1980
Tongue
German
Weight
722 KB
Volume
63
Category
Article
ISSN
0018-019X

No coin nor oath required. For personal study only.

✦ Synopsis

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.

📜 SIMILAR VOLUMES

3-Mercapto-4-phenyl-3-cyclobuten-1,2-dio
3-Mercapto-4-phenyl-3-cyclobuten-1,2-dion
✍ Dr. Arthur H. Schmidt; Prof. Dr. Walter Ried; cand. chem. Peter Pustoslemsek; Di 📂 Article 📅 1972 🏛 John Wiley and Sons 🌐 English ⚖ 181 KB 👁 1 views
3-Mercapto-4-phenyl-3-cyclobutene-1,2-di
3-Mercapto-4-phenyl-3-cyclobutene-1,2-dione
✍ Dr. Arthur H. Schmidt; Prof. Dr. Walter Reid; Peter Pustolemsek; Dipl.-Chem. Han 📂 Article 📅 1972 🏛 John Wiley and Sons 🌐 English ⚖ 297 KB 👁 2 views
Reaktionen mit Cyclobutendionen, VII. Üb
Reaktionen mit Cyclobutendionen, VII. Über die Umsetzung von 2-Hydroxy-1-phenyl-cyclobuten-(1)-dion-(3.4) mit aromatischen Aminen
✍ Ried, Walter ;Kunkel, Wolfgang ;Isenbruck, Günter 📂 Article 📅 1969 🏛 Wiley (John Wiley & Sons) 🌐 English ⚖ 225 KB 👁 1 views

Uber die Umsetzung von 2-Hydroxy-l-phenyl-cyclobuten-(l)diom(3.4) mit aromatischen Aminen Aus dem Institut fur Organische Chemie der Universitat Frankfurt am Main (Eingegangen am 3. Marz 1969) rn 2-Hydroxy-1-phenyl-cyclobutendion reagiert rnit primaren aromatischen Aminen zu 3-Anilino-1-phenyl-cyclo