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2,7‐Di‐ tert ‐butylnaphtho[1,8‐ cd ][1,2]dithiole 1,2‐dioxides: Thermally Stable, Photochemically Active vic ‐Disulfoxides
Author(s) -
Grainger Richard S.,
Patel Bhaven,
Kariuki Benson M.
Publication year - 2009
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200901788
Subject(s) - steric effects , epimer , chemistry , thermal , stereochemistry , photochemistry , medicinal chemistry , physics , thermodynamics
Bulking up: The thermal barrier to rearrangement of a vic ‐disulfoxide is significantly increased through steric buttressing about the (O)SS(O) bond. Whereas the title compounds represent the most thermally stable vic ‐disulfoxides known to date, they also undergo a novel photomediated epimerization at room temperature (see scheme).
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