Oxydation des alcènes par l'ion thallique. I. Stéréochimie et mécanisme de l'oxydation des cyclohexènes
1971 ◽
Vol 49
(15)
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pp. 2586-2589
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The stereochemistry of the diols obtained by oxidation of 3-t-butylcyclohexene by thallic sulfate indicates that the α hydroxyl group participates in the breaking of the C—T1 bond of the intermediate organothallous compound. The fact that only the trans diols are obtained indicates that an SN2 substitution of the thallium can be excluded. We suggest that the thallic oxidation in aqueous media of olefin of rigid conformation is an excellent one-step method of preparing trans diols. The formation of the trans diaxial diol upon oxidation of 4-t-butylcyclohexene tends to confirm that hypothesis.
1992 ◽
Vol 40
(11)
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pp. 2309-2314
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2006 ◽
Vol 36
(7)
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pp. 843-847
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2019 ◽
Vol 375
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pp. 122000
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2021 ◽
Vol 1734
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pp. 012019
2002 ◽
Vol 43
(21)
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pp. 3887-3890
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