The Reaction of Grignard Reagents with 3,4-Epoxy-1-Butene. II. Ethylmagnesium Bromide and Diethylmagnesium

Freedman, Robert W.; Becker, Ernest I.

doi:10.1021/jo50005a007

Cited by 13 publications

(3 citation statements)

References 11 publications

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“…It is reasonable, therefore, that addition of an aryl anion should be easier than rearrangement. (79,113), methylmagnesium bromide and isopropylmagnesium bromide (113), and 2-thienylmagnesium bromide (90).…”

Section: Ch3bmentioning

confidence: 99%

Mechanisms Of Epoxide Reactions

Parker¹,

Isaacs²

1959

Chem. Rev.

1,196

512

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Section: Ch3bmentioning

confidence: 99%

Mechanisms Of Epoxide Reactions

Parker¹,

Isaacs²

1959

Chem. Rev.

1,196

512

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“…A similar pathway was postulated by Fritel and FetizonSgO to explain the ready, albeit low-yield, cyclization of isopulegone oxide to a furan derivative, as shown in Eq. (579). The renowned sugar epoxide ' Brigl's anhydride '245 has been cleaved with a number of alcohols (Eq.…”

Section: R = H Chsmentioning

confidence: 99%

Ethylene Oxides

Rosowsky¹

1964

Chemistry of Heterocyclic Compounds: A Series of Monographs

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“…Diethylmagnesium and 3,4-epoxy-1-butene react to give a mixture of alcohols in 70 per cent yield. Fractionation separates only two products: namely, 2-hexenl-ol (26 per cent) and 2-ethyl-3-buten-1 -ol (74 per cent) (71). With ethylmagnesium bromide the overall yield of alcohols was ca.…”

Section: Ch2cich-ch2mentioning

confidence: 99%