C/s-2-octene

We now have to consider how to convert the C8 materials that we might make into c/s-2-octene. The possibilities are ... 

Octene, 567 rro s-3-Octene, 577 c/s-4-Octene-l, 7-diyne, 913 tra s-4-Octene epoxide, 1192... 

This analysis suggests that in the double cross experiment the product of [Ci4]/[Ci2]—called —and [Ci4]/[Cig]—called rz—should be 4, and Fig. 1 shows that experimentally this is approximately true. A more accurate measure of this product at zero time can be achieved by multiplying ri and rj at the different times and extrapolating to zero time, as in Fig. 3. In a series of four such experiments, three using cyclooc-tene, c/s-2-butene, and cw-4-octene, and one using cyclooctene, trans-2-butene, and tra j-4-octene, the average value of ri x /-z at zero time was measured as 4.05 0.05 (66). 

The relative rates of lithium 2-aminoethylamide-catalyzed isomerization of /r Azs-4-octene, c/ s-4-octene, and 1-octene in ethylene diamine solutions at 25°C are 1, 3.5, and 90. Cw-2-octene was the major product from 1-octene, while trans- and m-3-octene were the principal initial products from cis- and /rtzAZ5-4-octene, respectively. 

Scheme 2.201. Synthesis of c/s-bicyclo[3.3.0]octenes via domino carbolithiation/ electrocyclization/electrophile trapping.

Olefin styrene, a-methylstyrene, frans-p-methylstyrene, 1-hexene, c/s and frans-4-octene, c-pentene, c-hexene, c-heptene, indene, 1,2-dihydronaphthalene... 

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