Add time:07/14/2019         Source:sciencedirect.com

The stereochemistry of syn and anti-forms of bridged bicyclo[3.n.1]-2-ene, tricyclo[7.n.1.0]-2-ene (n=1–3) and bicyclo[4.3.1]dec-7-ene derivatives can be assigned from the 13C chemical shift difference of the double bond. Both syn-9-R-bicyclo[3.3.1]non-2-enes and syn-13-R-tricyclo[7.3.1.02,7]tridec-2(7)-enes have a large shielding difference between sp2 carbons, while the corresponding anti-forms have a smaller one. In contrast, 8-R-bicyclo[3.2.1]oct-2-enes and 12-R-tricyclo[7.2.1.02,7]dodec-2(7)-enes have an inverse correlation. The reason of this specificity is the influence of the γ-gauche effect on the chemical shift of C(2) atom. The GIAO theory has been applied to investigate the 13C chemical shifts. The conformational equilibrium in the formamide group of 13-formylamino-tricyclo[7.3.1.02,7]tridec-2(7)-enes has been studied.

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