Question

Under normal circumstances, tertiary alcohols are not oxidized. However, when the tertiary alcohol is allylic, it can undergo a migration of the double bond (called an allylic shift) and subsequent oxidation of the alcohol. A particularly effective reagent for this reaction is Bobbitt’s reagent, similar to TEMPO used in many oxidations. (M. Shibuya et al., J. Org. Chem., 2008, 73, 4750.)

Show the expected product when each of these 3° allylic alcohols is oxidized by Bobbitt’s reagent.

(a)

(b)

(c)

(d)

Short answer

The organic reagent that bears nitrogen and ketone groups and exists in salt form is Bobbitt’s reagent.

This compound is invented by James M. Bobbitt. This reagent is used for the preparation of alkaloids namely salsoline, carnegine, salsolidine, and lophocerine.

Step-by-step solution

About Bobbitt’s reagent

The organic reagent that bears nitrogen and ketone groups and exists in salt form is Bobbitt’s reagent.

This compound is invented by James M. Bobbitt. This reagent is used for the preparation of alkaloids namely salsoline, carnegine, salsolidine, and lophocerine.

Reaction of the first compound with Bobbitt’s reagent

A carbonyl group will be generated in the ring, and the double bond shift takes place. The OH group will be removed and the reaction is shown below.

Reaction of the second compound with Bobbitt’s reagent

A carbonyl group will be generated and the double bond shift takes place. The OH group will be removed and the reaction is shown below.

Reaction of the third compound with Bobbitt’s reagent

There will be the generation of a carbonyl group and the double bond shift takes place. The OH group will be removed. The reaction is shown below.

Reaction of the fourth compound with Bobbitt’s reagent

A carbonyl group will be generated and a double bond shift takes place. The OH group will be removed and the reaction is shown below.