Trifluoromethanesulfonic acid → Benzene, (1-cyclopropylethyl)-

HRID 1089608Notes

Reaction equation

[CH:1]1([C:4]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[CH2:5])[CH2:3][CH2:2]1.C(S(O)(=O)=O)(F)(F)F>>[CH:1]1([CH:4]([C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH3:5])[CH2:3][CH2:2]1

Participants

Reactant 2

HCID 62406Trifluoromethanesulfonic acid

HCID 70000alpha-Cyclopropylstyrene

Product 1

HCID 317702Benzene, (1-cyclopropylethyl)-Yield 58%

Procedure

A solution of α-cyclopropylstyrene (5 microliters, 0.033 mmol) and (C5H5)(CO)3MoH (24 mg, 0.097 mmole) in dichloromethane-d2 was treated at room temperature with CF3SO3H (3 microliters, 0.034 mmol). A color change indicated an immediate reaction and an 1H NMR after 5 minutes showed that α-cyclopropyl-ethylbenzene (58% yield) was the major product. This indicates that hydrogenation of the carbon-carbon double bond is favored over cleavage of the cyclopropyl group. Additional CF3SO3H (5 microliters, 0.056 mmol) was added. NMR after one hour showed the major product to be 2-phenylpentane (Ca 57%). Two other products, 3-phenylpentane and β-methyl-butylbenzene, were observed in approximate yields of 14% and 7% respectively. These two products are formed due to rearrangement of the intermediate carbocation which is formed from the reaction of CF3SO3H with α-cyclopropyl-ethylbenzene.

Workup

customan immediate reaction

Sources & evidence

ORD record: ord-c860998df96e482c8fa50ba282263ac5
Source dataset: uspto-grants-1990_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04967031

Reaction notes

Loading…