Conformation and barrier to inversion of a 12-membered heterocycle containing two disulfide bonds |
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Authors: | Zev Lidert |
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Affiliation: | Division of Organic Chemistry 1, Chemical Center, University of Lund, Lund, Sweden |
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Abstract: | Raman and 1H NMR spectroscopic data obtained for a dimeric product 4c formed on iodine oxidation of N-pnenyl-N-thiomethyl-thioglycolic acid amide (3c) indicate that this product is 4,11-diphenyl-4,11-diaza-1,2,7,8-tetrathia-cyclododecane-5,10-dione. The barrier to interconversion between the conformers of 4c has been determined by DNMR. The height of the barrier (ΔG≠ = 17.3 ±0.1 ) is in agreement with the proposed structure. This investigation thus gives a support to the previously proposed mechanism of regiospecific dimeric oxidations of unsymmetrical dithols of type 3c. |
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