1-Bromoadamantane → Adamantane

Participants

Reaction Steps

Illustrative examples of the uses of one of these fluorous tin reagents, (C6F13CH2CH2)3SnH, are shown in FIG. 2. Reduction of adamantyl bromide with 1 equiv of (C6F13CH2CH2)3SnH followed by fluorous-organic liquid-liquid extraction provides the organic product adamantane on evaporation of the organic liquid phase and the fluorous product (C6F13CH2CH2)3SnBr on evaporation of the fluorous phase. A similar reduction can be conducted in a more economical way by using a catalytic amount of the fluorous tin hydride along with an inexpensive inorganic reductant like sodium cyanoborohydride. A three-phase liquid extraction then provides the respective products: inorganic salts (from the aqueous phase), adamantane (from the organic phase), and the tin hydride catalyst (from the fluorous phase).

Provenance & Evidence