Substituent effects on cyclobutyl and cyclopropylcarbinyl cations
The acetolyses of 3-substituted cyclobutyl tosylates (X = Ar, Cl, and OEt) were examined giving rate constants and product distributions. With the alkyl- and aryl-substituted compounds, the rate-determining step leads to the formation of a bridged cyclobu
Wiberg, Kenneth B.,Shobe, David,Nelson, Gordon L.
p. 10645 - 10652
(2007/10/02)
HOMOALLYLIC SUBSTITUTION REACTIONS OF LITHIUM DIALKYL CUPRATES WITH CYCLOPROPYLCARBINYL HALIDES: MECHANISTIC CONSIDERATIONS
Highly reactive lithium dialkyl cuprates and 1-bromo-1-cyclopropylalkanes, 4, react to give good yields of the homoallylic substitution product, 6.Less reactive organocuprates react with 4 to give mixtures of 6 and the direct substitution product 7.These results are consistent with a copper(I) radical intermediate which undergoes facile rearrangement prior to reductive coupling.
Hrubiec, Robert T.,Smith, Michael B.
p. 1457 - 1468
(2007/10/02)
CYCLOPROPYLCARBINYL COMPOUNDS FROM HOMOALLYLIC IODIDES
A simple synthesis of cyclopropylcarbinyl compounds based on the reaction of homoallylic iodides with silver salts in anhydrous medium is described.
Previtera, Lucio,Monaco, Pietro,Mangoni, Lorenzo
p. 1293 - 1294
(2007/10/02)
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