Methyleneketenes and methylenecarbenes. X. Precursors for the generation of methyleneketene and deuterated methyleneketenes for microwave spectroscopy

Authors:
  • GBGl Blackman
    Gl Blackman
  • RBRd Brown
    Rd Brown
  • RBRfc Brown
    Rfc Brown
  • FEFw Eastwood
    Fw Eastwood
  • GMGL McMullen
    GL McMullen
  • MRMl Robertson
    Ml Robertson
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Abstract
The synthesis of a mixture of deuterated cyclopentadiene adducts (3) required for the pyrolytic generation of CHD=C=C=O and CD2=C=C=O is described. Methyleneketene is conveniently generated for microwave spectroscopy by flash vacuum pyrolysis of acrylic anhydride at 510- 560°. Pyrolysis of diphenylmethyl propiolate gives benzophenone and methyleneketene (or its decomposition products)as the major process, but minor processes leading to diphenylmethane, fluorene and 3-phenylphthalide also occur.