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Upstream product

• 256512-75-1 (3aR,9aR,9bS,R_S)-1,3,3a,4,6,7,8,9,9a,9b-decahydro-5-[(1S)-isoborneol-10-sulfinyl]-2-phenylbenz[e]isoindole-1,3-dione 
• 256512-82-0 (3aR,9aR,9bS,R_S)-1,3,3a,4,6,7,8,9,9a,9b-decahydro-5-[(1S-exo)-2-bornylsulfinyl]-2-phenylbenz[e]isoindole-1,3-dione 

Relevant academic research and scientific papers

An investigation of the behaviour of α,β-unsaturated sulfoxides in the presence of trimethylsilyl iodide

A mild, efficient and seemingly general method for converting α,β-unsaturated sulfoxides into carbonyl compounds by means of trimethylsilyl iodide (TMSI) is described. Experiments on different substrates and trimethylsilyl halides lead to the conclusion that the oxidation state of the sulfur atom, on one hand, and halogen kind in TMSX on the other, assume a determining role in the progression of the reaction. The ease of experimental procedure, the possibility of 1H NMR monitoring, and good yields of final products constitute advantages of the TMSI-promoted conversion of α,β-unsaturated sulfoxides into carbonyl compounds.

Unexpected conversion of vinyl sulfoxides into carbonyl compounds by means of iodotrimethylsilane

The unexpected and previously unknown TMSI-promoted conversion of α,β- unsaturated sulfoxides into carbonyl compounds and disulfides is described. It occurs in good yields under mild conditions. The examples provided support the generality and efficiency of this procedure which acts as a good method for removing the sulfinyl group with the advantage of transforming the vinyl sulfoxides into carbonyl compounds. (C) 2000 Elsevier Science Ltd.