Tris(thiocyclopropanone)

Abstract

NotesYol. 27 colorless needles separated at once; yield, 4.0 g. (93%).Sublimation in vacuo gave faintly yellow, sturdy crystals, m.p. 189-190°. A mixture melting point determination with the material prepared by method A showed no depression, and infrared spectra were identical.Treatment of the Complex (IV) with Acetic Anhydride.-A mixture of 1.1 g. of IV, 8 ml. of acetic anhydride, and 10 ml. of pyridine was heated on a steam bath for 40 min. and then evaporated to dryness under reduced pressure.Treatment of the crystalline residue with about 60 ml. of pentane and filtration gave a solid which was recrystallized from carbon tetrachloride to yield 0.46 g. (60%) of long needles, m.p. 115-120°. Sublimation raised the melting point to 118-120°. Diacetylhydroquinone is reported to melt at 123°.10The infrared spectrum of the sublimed material [Nujol mull, principal bands at 5.49 (w), 5.67 (s), 5.80 (sh), and 6.66 µ] was identical with the spectrum of an authentic sample of hydroquinone diacetate.The pentane filtrate was concentrated to a small volume, cooled, and filtered to give a solid (m.p. 91-104°) which was sublimed in vacuo to give 0.45 g. (70%) of 2,3-dimethylquinoxaline, m.p. 103-104°( lit.,11 m.p. 106°). Its infrared spectrum was identical with the spectrum of an authentic sample of 2,3-dimethylquinoxaline.Treatment of the Complex (IV) with Potassium Permanganate.-To a stirred mixture of the complex in aqueous acetone was added solid potassium permanganate until the purple color just persisted. The manganese dioxide was removed by filtration and rinsed with water followed by acetone, and the filtrate was extracted twice with ether.

Three-Membered-Ring-Based Molecular Architectures

“…4,8,12-Trithiatrispiro[2.1.2.1.2.1]dodecane ( 796 ), the cyclic trimer of thiocyclopropanone is the first member of a larger family of [ n ]rotanes 798 expanded with heteroatoms, which all are essentially cyclic oligomers of cyclopropanone, cyclopropanethione, and cyclopropanimine, respectively. Compound 796 was prepared by 3-fold γ-dehydrochlorination of compound 795 with potassium amide in 75% yield (Scheme ) . Later on, a general approach to compounds of type 798 by condensation of cyclopropanone derivatives 797 and 799 was elaborated (Scheme ) .…”

ChemInform Abstract: Selective Cleavage of Asymmetric Acetals to Hemiacetal Acetates. Ring Opening of Chlorinated 2‐Alkoxytetrahydrofuran and ‐tetrahydropyran Derivatives.

“…'H NMR t-like 8 Hz; 3.87 (1H) dq 9 Hz 7 Hz; 4.51 (IH) s. " C NMR (CDCl3) : 6 15.2 corr. 6 (C-2); corr. 6 5.91 (C-1); 170.1 (OAc).…”

“…(C-5); m c o r r . 6 6.15 (C-2); (OAc). Hz; 6.9 Hz; 4.44 (1H) dt 11.6 Hz; 6.9 Hz; 5.91 (1H) s. ' C NMR (CDCb) : 6 20.8 corr.…”