The 16-electron electrocyclisation of vinylogous heptafulvalene

Bingmann, H.; Knothe, Lothar; Hunkler, Dieter; Prinzbach, Horst

doi:10.1016/s0040-4039(01)86501-1

Cited by 4 publications

(1 citation statement)

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“…The 16~-electron vinylogous heptafulvene (55) 51 cyclizes thermally in a conrotatory manner to give compound (56). Whilst this is the stereochemistry expected for an 'orbital-symmetry-controlled' process, the related l4r-electron and 12~-electron compounds (57)52 and (58)53 also cyclize in a conrotatory sense, despite the fact…”

Section: Memcnmentioning

confidence: 99%

Chapter 4. Reaction mechanisms. Part (i) Pericyclic reactions

Bushby¹

1979

Annu. Rep. Prog. Chem., Sect. B

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The pericyclic reactions of singlet oxygen' and of the photoexcited states of organic anions2 have been reviewed.The effect of substituents on pericyclic reactions has long remained a source of difficulty. This year two interesting approaches to the problem have been described. Carpenter and Wilcox3 have used a simple HMO model. They have shown that for electrocyclic reactions, 1,5-hydrogen shifts, cyclopropane stereomutations, and reactions involving carbon-carbon bond homolysis, there is a linear relationship (1) between AAH* (the measured effect of the substituent on the enthalpy of activation in kcal mol-l) and AAE, (the calculated difference between the effect of the substituent on the HMO .rr-energy of the substrate and that of a suitable model for the transition state, both in units of p. Mobius cyclobutadiene is taken as a model for the transition state in the conrotatory opening of cyclobutene).

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Section: Memcnmentioning

confidence: 99%