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Two-way cycloaddition of fluoro-olefins to propadiene

โœ Scribed by D.R. Taylor; M.R. Warburton

Publisher
Elsevier Science
Year
1967
Tongue
French
Weight
191 KB
Volume
8
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

Cycloaddition reactions between an allene and a ketone or unsymmetrically substituted olefin CH2:CHX (where X = CN, C02H, C02CH3, CHO, etc.) have hitherto been reported to give only one of the two possible 1:l adducts, the structures of which were shown to be, respectively, 24lkylideneoxetans (1) and 3-substituted methylenecyclobutanes (2). We have found that thermal co-dimerisation of propadiene with an unsymmetrical fluoro-olefin aaaucts (I a,b; II a,b). CF2:CClX (where X = F or Cl) gives both possible Cl,uF2

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## Abstract Selected [2+2]โ€cycloadditions of three alkylvinylketenes **2** to one monoโ€ and seven dialkylโ€olefins **3** yielded eleven 2โ€alkylโ€2โ€vinylcyclobutanones **4** __(Tables 1__ and __2).__ Three methods were compared, all involving __in situ__ generation of the ketenes **2** by HClโ€eliminat