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Internal photolytic 2+2 cycloaddition of the cyclooctatetraene-dimethyl acetylenedicarboxylate adduct

โœ Scribed by S.F. Nelsen; J.P. Gillespie

Publisher
Elsevier Science
Year
1969
Tongue
French
Weight
97 KB
Volume
10
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

The recent publication of Miller and Hedaya' on the photochemistry of 7,8dicarbomethoxytricyclo[4.2.2.0 2J5]deca-3,7,q-triene (1) leads us to report our rather different results. They found that 1 gave dimethyl phthalate, syn-tri-cycloC4.2.0.0 2J5]octa-3,7-diene (2), and cyclooctatetraene upon photolysis at room temperature, -20ยฐ, and liquid nitrogen temperature. That 2 arises from cyclobutadiene was deduced from isolation of cyclobutadiene-diene adducts, and decreased yields of 2, in the presence of piperylene or isoprene. They report looking for thermally labile 7,8-q,lO closure product 1 at -20ยฐ, but observe no closure.

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Pd(0)-catalyzed selective [2 + 2 + 2] cycloaddition of dimethyl nona-2,7-diyne-1,9-dioate derivatives with dimethyl acetylenedicarboxylate
โœ Yoshihiko Yamamoto; Asako Nagata; Kenji Itoh ๐Ÿ“‚ Article ๐Ÿ“… 1999 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 245 KB

In the presence of 2.5 mol % of Pd2(dba) 3 and 5 tool % ofPPh 3, nearly eqcimolar mnounts of dimathyl nona-2,7-diyne-1,9-dioate derivatives and dimethy! acetylenedicarboxylate (DMAD) were reacted in toluene at 110 "C to give indan, phthalin, a~d isoindoline derivatives selectively in moderate to goo