1-Bromoadamantane → Adamantane

HRID 982910Notes

Reaction equation

HRID 982910 reaction equation
[Sn].[SnH](CCC(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(CCC(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)CCC(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F.[C:66]12(Br)[CH2:75][CH:70]3[CH2:71][CH:72]([CH2:74][CH:68]([CH2:69]3)[CH2:67]1)[CH2:73]2>>[CH:66]12[CH2:75][CH:70]3[CH2:71][CH:72]([CH2:74][CH:68]([CH2:69]3)[CH2:67]1)[CH2:73]2

Participants

4

Reactant 3

HCID 791061-BromoadamantaneHCID 2733169Tris((perfluorohexyl)ethyl)stannane2×HCID 5352426Tin atom

Product 1

HCID 9238Adamantane

Procedure

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).

Sources & evidence

ORD record
ord-a611a96704ea4d9c853827fd79ea59eb
Source dataset
uspto-grants-2005_03
Patent number
US06861544B1

Reaction notes

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