Publications [#233488] of Andrew T. McPhail

Journal Articles

  1. Quinu, LD; Leimert, J; Middlemas, ED; Miller, RW; McPhail, AT, "3, 8-Thionanedione 1, 1-Dioxide. Synthesis and Solid-State Conformation", Journal of Organic ChemistryJanuary,, 1979, 44(20), 3496-3500, American Chemical Society (ACS) [Gateway.cgi], [doi].
    (last updated on 2026/01/21)

    Abstract:
    The title compound is conveniently prepared in 80% overall yield by ozonolysis at -78 °C of the cycloadduct of S02 with 1, 2-dimethylenecyclohexane. Single-crystal X-ray analysis establishes that the nine-membered ring adopts a twist-chair-chair conformation in which the sulfur atom and the midpoint of the C(5)-C(6) bond lie on a noncrystallographic C2 axis, but the ring shape differs significantly from that of cyclononane in order to accommodate transannular dipole-dipole interactions. Crystals are orthorhombic, space group P212121, with a = 8.963 (4) Å, b = 15.403 (7) Å, c = 6.724 (3) Å, and Z = 4. Atomic positional and thermal parameters were refined by full-matrix least-squares calculations to R = 0.032 over 913 statistically significant reflections. © 1979, American Chemical Society. All rights reserved.