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Chemical Compound Review:

Tropiliden cyclohepta-1,3,5-triene

Synonyms: Tropyliden, Tropilidene, Tropilidine, ACMC-1ALO0, C99205_ALDRICH, ...

Salpin, J.Y. et al., Sukcharoenphon, K. et al., Kimura, T. et al., Sugimura, T. et al.

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High impact information on Tropilidine

Novel metal-free hydrogenation of the carbon-carbon double bond in azulenoid enones by use of cycloheptatriene and protic acid [1].
Oxidative addition of the sulfur-sulfur bond of 2,2'-pyridine disulfide (C(5)H(4)NS-SC(5)H(4)N) with L(3)W(CO)(3) [L = pyridine, (1)/(3)CHPT; CHPT = cycloheptatriene] in methylene chloride solution yields the seven-coordinate W(II) thiolate complex W(eta(2)-mp)(2)(CO)(3) (mp = monoanion of 2-mercaptopyridine) [2].
Ab initio calculations are in agreement with these experimental values if the 1,2-dihydrotropylium tautomer, [CHT + H((1))](+), generated by protonation of CHT at C-1, is assumed to be the conjugate acid, resulting in PA(CHT) = 825 +/- 2 kJ mol(-1) and deltaH(f)(0)(300)([CHT + H((1))](+)) = 892 +/- 2 kJ mol(-1) [3].

Biological context of Tropilidine

Asymmetric synthesis of deoxypolypropionate units via stereoselective hydrogenation of optically active cycloheptatriene [4].

Associations of Tropilidine with other chemical compounds

However, the calculations indicate that protonation of cycloheptatriene at C-2 gives rise to transannular C-C bond formation, generating protonated norcaradiene [NCD + H](+), a valence tautomer being 19 kJ mol(-1) more stable than [CHT + H((1))](+) [3].

References

Novel metal-free hydrogenation of the carbon-carbon double bond in azulenoid enones by use of cycloheptatriene and protic acid. Kimura, T., Takahashi, T., Nishiura, M., Yamamura, K. Org. Lett. (2006) [Pubmed]
Synthesis and structure of W(eta(2)-mp)(2)(CO)(3) (mp = monoanion of 2-mercaptopyridine) and its reactions with 2,2'-pyridine disulfide and/or NO to yield W(eta(2)-mp)(4), W(eta(2)-mp)(2)(NO)(2), and W(eta(2)-mp)(3)(NO). Sukcharoenphon, K., Capps, K.B., Abboud, K.A., Hoff, C.D. Inorganic chemistry. (2001) [Pubmed]
The gas-phase basicity and proton affinity of 1,3,5-cycloheptatriene--energetics, structure and interconversion of dihydrotropylium ions. Salpin, J.Y., Mormann, M., Tortajada, J., Nguyen, M.T., Kuck, D. European journal of mass spectrometry (Chichester, England) (2003) [Pubmed]
Asymmetric synthesis of deoxypolypropionate units via stereoselective hydrogenation of optically active cycloheptatriene. Sugimura, T., Sato, Y., Im, C.Y., Okuyama, T. Org. Lett. (2004) [Pubmed]

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