2568-76-5Relevant articles and documents
SYNTHESIS AND PROPERTIES OF 3,3-DISUBSTITUTED CYCLOPROPENES CONTAINING AN ALKYNYL GROUP
Ivanov, A. L.,Domnin, I. N.
, p. 2298 - 2303 (2007/10/02)
3-Methyl-3-ethynylcyclopropene, 3-methyl-3-(3,3-dimethylbutynyl)cyclopropene, and bis(1-methyl-2-cyclopropenyl)acetylene were obtained by the reaction of the corresponding alkenynes with dibromocarbene following by partial reduction of the dibromide and elimination of hydrogen bromide in the monobromide.It was shown by 13C NMR spectroscopy that the introduction of an alyknyl group in place of the methyl group at position 3 of the three-membered ring leads to an increase in the s character of the carbon atoms at the cyclopropene double bond.At elevated temperatures 3-methyl-3-ethynylcyclopropene undergoes cyclodimerization with the formation of a mixture of the following stereoisomers: 3e,6e-Dimethyl-3a,6a-diethynyl-trans-tricyclo2.4>hexane, 3e,6a-dimethyl-3a,6e-diethynyl-trans-tricyclo2.4>hexane, and 3a,6a-dimethyl-3e,6e-diethynyl-trans-tricyclo2.4>hexane.