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Synthesis and Reactivity of 4-chloro-3,3,4-trifluoro-methoxycarbonyl Cyclobutene (ctmc)

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Plancquaert, MA. Janousek, Z. Viehe, HG.

An improved synthesis of CTMC is described. This cyclobutene is thermally stable towards electrocyclic ring opening. Its reactivity is explored and a number of radical adducts are described. A more complicated picture is observed with various nucleophiles. The strong dienophilic character of CTMC is illustrated by numerous examples. CTMC reacts well as a dipolarophile with diphenylnitrone, diphenylnitrilimine and diazoalkanes. The high reactivity of this cyclobutene is due to its inherent polarity and strain.

Document type Article de périodique (Journal article) – Article de recherche
Publication date 1994
Language Anglais
Journal information "Journal fuer Praktische Chemie. Chemiker-Zeitung" - Vol. 336, no. 1, p. 19-28 (1994)
Peer reviewed yes
Publisher Johann Ambrosius Barth Verlag (Heidelberg)
issn 0941-1216
Publication status Publié
Affiliation UCL
Links
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Bibliographic reference Plancquaert, MA. ; Janousek, Z. ; Viehe, HG.. Synthesis and Reactivity of 4-chloro-3,3,4-trifluoro-methoxycarbonyl Cyclobutene (ctmc). In: Journal fuer Praktische Chemie. Chemiker-Zeitung, Vol. 336, no. 1, p. 19-28 (1994)
Permanent URL http://hdl.handle.net/2078.1/49165