An Unprecedented Biradical Cyclization as an Alternative Pathway to the Myers–Saito Cycloaromatization in the Thermal Reactions of Enyne Allenes

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All enyne allenes described in this paper were prepared from the corresponding propargyl alcohols by rearrangement in the presence of chlorodiphenylphosphane. All starting materials and products were isolated as pure compounds and fully characterized by1H 13C and31P NMR spectroscopy mass spectrometry and IR spectroscopy (see Table 2).

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The relative configuration is determined by the three contiguous sterogenic units: the stereogenic axis of the allene and the stereogenic centers in the cyclopropyl ring C*H and C*HPh.

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(a) Since our first report on a C2–C6cyclization two other papers have been published [17b c] that report on a similar reaction leading to benzofulvene derivatives. However in these cases owing to the substitution patterns a zwitterionic intermediate seems to be more plausible than a biradical.

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