P. A. T. W. Porskamp

Complete asymmetric inductions in diels-alder reactions of chiral sulfines

Abstract Complete asymmetric induction was observed during the cycloaddition reaction of 2,3-dimethyl-1,3-butadiene with chiral, camphor or sulfoximino substituted, sulfines.

Structure and absolute configuration of 10-chloro-10-sulfinylcamphor, C10H13ClO2S

The structure of the title compound, C10H13ClO2S, was determined by X-rays:Mr=232.72, monoclinic, space groupP21,a=6.4902(6),b=12.022(1),c=14.130(3) Å,β=103.11(1)°,Vc=1073.7 Å3,Z=4,Dx=1.44 Mg m−3. MoKα radiation (graphite crystal monochromator, λ=0.71069 Å),μ(MoKα)=4.9 cm−1,F(000)=342,T=293 K. Final conventionalR-factor=0.035 for 2221 observed reflections and 252 variables. The structure was solved usingDirdif. The absolute configuration of the structure is reported. The two independent molecules differ primarily in the orientation of the sulfine group with respect to the camphor moiety.

Crystal and molecular structure of 3,6-dihydro-4,5-dimethyl-2-[2-(methoxymethyl)pyrrolydinesulfonyl]-2-phenyl-2H-thiapyran-1-oxide, C19H27NO4S2

The crystal structure of a dihydrothiapyranS-oxide was determined from single-crystal diffractometer data, C19H27NO4S2, MoKα radiation: orthorhombic, space groupP212121, usinga=8.9604(10),b=13.5928(15),c=16.5621(19) Å,z=4. The molecule has theE-geometry, and the absolute configuration isR at C1 andS at S1.

SYNTHESIS OF SULFINES BY ALKYLIDENATION OF SULFUR DIOXIDE

Abstract The most important route for the preparation of sulfines (thione-oxides) thusfar is that involving the oxidation of thiocarbonyl containing compounds with peroxycarboxylic acid. A new challenging approach to the synthesis of sulfines is the alkylidenation of sulfur dioxide.