Peracetic Acid → 4a,7-Methano-4aH-naphth[1,8a-b]oxirene, octahydro-4,4,8,8-tetramethyl-

HRID 413557Notes

Reaction equation

HRID 413557 reaction equation
[CH3:1][C:2]1([CH3:15])[C:7]23[CH2:11][CH:10]([C:12]([CH3:14])([CH3:13])[C:6]2=[CH:5][CH2:4][CH2:3]1)[CH2:9][CH2:8]3.C(OO)(=[O:18])C>>[CH3:1][C:2]1([CH3:15])[C:7]23[CH2:11][CH:10]([C:12]([CH3:14])([CH3:13])[C:6]42[O:18][CH:5]4[CH2:4][CH2:3]1)[CH2:9][CH2:8]3

Participants

3

Reactant 2

HCID 6585Peracetic AcidHCID 1025622H-2,4a-Methanonaphthalene, 1,3,4,5,6,7-hexahydro-1,1,5,5-tetramethyl-, (2S)-

Product 1

HCID 1070354a,7-Methano-4aH-naphth[1,8a-b]oxirene, octahydro-4,4,8,8-tetramethyl-

Procedure

In the first stage, isolongifolene (1) can be reacted in a known manner, for example with peracetic acid, to give isolongifolene oxide (2) (Tetrahedron Lett. 1964, 8, 417; J. Org. Chem. 1970, 35, 1172).

Sources & evidence

ORD record
ord-23c61cac9e6d4f11852bd95e4e78c379
Source dataset
uspto-grants-2003_05
Patent number
US06566562B2

Reaction notes

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