Thiofenchone → (+-)-Fenchone

HRID 1164694Notes

Reaction equation

HRID 1164694 reaction equation
[CH3:1][C:2]1([CH3:11])[C:8](=S)[C:6]2([CH3:10])[CH2:7][CH:3]1[CH2:4][CH2:5]2.C[O:13]C1C=CC([Te](C2C=CC(OC)=CC=2)=O)=CC=1>>[CH3:1][C:2]1([CH3:11])[C:8](=[O:13])[C:6]2([CH3:10])[CH2:7][CH:3]1[CH2:4][CH2:5]2

Participants

3

Reactant 2

HCID 136682ThiofenchoneHCID 3044917Bis(p-methoxyphenyl) telluroxide

Product 1

HCID 14525(+-)-FenchoneYield 23%

Procedure

Thiofenchone (23 mg, 0.14 mmol) was reacted with bis-(p-methoxyphenyl)telluroxide for 42 h. Fenchone (5 mg, 23%) νmax 1965,1930,1875,1742,1465,1385 and 1025 cm-1 was obtained after p.l.c. (petroleum ether-ethyl acetate 20:1). A low yield was obtained due to volatility of the product. Sulphur and bis-(p-methoxyphenyl)telluride were, however, isolated in 75 and 81% yields respectively.

Sources & evidence

ORD record
ord-46f188a4f2c349e29009205b486c5935
Source dataset
uspto-grants-1983_01
Patent number
US04370497

Reaction notes

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