Babler-Dauben Oxidation
1.6 هزار بار بازدید -
3 سال پیش
-
The Babler-Dauben Oxidation is the
The Babler-Dauben Oxidation is the catalytic chromium-mediated 1,3-oxidative transposition of allylic alcohols.
General features:
1. The reaction produces the desired enone product in high yields, and it doesn't require air-free conditions nor heating.
2. A common solvent is anhydrous DCM or chloroform.
3. The main drawback is the use of the highly toxic oxidizing agent, PCC.
4. Besides, the Babler-Dauben oxidation of secondary allylic alcohols proves more difficult to control than that of tertiary analogues.
Reaction mechanism:
1. The cyclic tertiary allylic alcohol adds to pyridinium chlorochromate, PCC, to form the corresponding chromate ester.
2. 1,3-oxidative transposition affords the 3-alkyl α,β-unsaturated ketone.
References:
https://nrochemistry.com/babler-daube...
Seminal publications:
1. Tetrahedron Letters. 57 (35): 3954–3957. doi:10.1016/j.tetlet.2016.07.076
2. Synthetic Communications. 6 (7): 469–474. doi:10.1080/00397917608082626
General features:
1. The reaction produces the desired enone product in high yields, and it doesn't require air-free conditions nor heating.
2. A common solvent is anhydrous DCM or chloroform.
3. The main drawback is the use of the highly toxic oxidizing agent, PCC.
4. Besides, the Babler-Dauben oxidation of secondary allylic alcohols proves more difficult to control than that of tertiary analogues.
Reaction mechanism:
1. The cyclic tertiary allylic alcohol adds to pyridinium chlorochromate, PCC, to form the corresponding chromate ester.
2. 1,3-oxidative transposition affords the 3-alkyl α,β-unsaturated ketone.
References:
https://nrochemistry.com/babler-daube...
Seminal publications:
1. Tetrahedron Letters. 57 (35): 3954–3957. doi:10.1016/j.tetlet.2016.07.076
2. Synthetic Communications. 6 (7): 469–474. doi:10.1080/00397917608082626
3 سال پیش
در تاریخ 1400/05/09 منتشر شده
است.
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