Β- AND Δ-Truxinic ACIDS

Freedman, M. S.; Mohadger, Y.; Rennert, J.; Soloway, Saul; Waltcher, I.

doi:10.1080/00304946909458397

Cited by 11 publications

(3 citation statements)

References 3 publications

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“…nate. 16 The photolysis of BDC produces predominantly 6-truxinate with a smaller contribution from 0-truxinate.17 The NMR spectra of the major products were in both cases consistent with the above assignments.…”

Section: Methodsmentioning

confidence: 58%

Photocycloaddition in liquid ethyl cinnamate and in ethyl cinnamate glasses. The photoreaction as a probe into the micromorphology of the solid

Egerton¹,

Hyde²,

Trigg³

et al. 1981

J. Am. Chem. Soc.

111

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Section: Methodsmentioning

confidence: 58%

Photocycloaddition in liquid ethyl cinnamate and in ethyl cinnamate glasses. The photoreaction as a probe into the micromorphology of the solid

Egerton¹,

Hyde²,

Trigg³

et al. 1981

J. Am. Chem. Soc.

111

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“…The 1 H and 13 C NMR spectral data of the tetraester 20 were consistent with a single, highly symmetrical cyclobutyl photodimer, but a distinction between the four possible isomers (α-truxillate, δ-truxinate, β-truxinate, and ε-truxillate) could not be made. The four isomers noted above for the methyl cinnamate photodimerization series were prepared by literature procedures to facilitate independent stereochemical and regiochemical assignment of 20 . In addition, further naphthoate/cinnamate isomeric photodimers were prepared by irradiation of a dilute benzene solution of dimethyl ester 9 at 300 nm, Scheme .…”

Section: Resultsmentioning

confidence: 99%

Toward Covalently Linked Organic Networks: Model Studies and Connector Syntheses

et al. 1997

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A model 1-naphthoic acid bearing a peri-positioned cinnamic acid residue crystallizes as a closed H-bonded dimer. Irradiation of this crystalline solid provides an α-truxillate-type cyclobutane photodimer in quantitative yield. Further synthesis studies have led to more highly functionalized naphthoic/cinnamic acid species capable of (pseudo)centrosymmetric attachment to polyvalent hubs. This system demonstrates the feasibility of designing a covalent molecular connector whose orientation is encoded by its H-bonding pattern.

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“…(7) Major mesylate: 1H NMR (C6D6) 1.34 (d, 3 H, J9 10 = 6.5 Hz, H10), 2.67 (dd, 1H, Je7= 1.8 Hz, J7 9 = 4.5 Hz, H7), 4.80 (dq, 1 H, J9 10 = 6.5 Hz, J7 9 = 4.5 Hz, H9). Minor mesylate: 1H NMR 1.30 (d, 3 H, J9 10 = 6.5 Hz, H10), 2.61 (dd, 1 H, J67 = 1.8 Hz, J79 = 8.0 Hz, H7), 4.82 (dq, 1 H, J9 10 = 6.5 Hz, J7,9 = 8.0 Hz, H9). (8) Ene-lactam from major mesylate: 1H NMR (CDCI3) 2.00 (d, 3 H, J = 7.5…”

mentioning

confidence: 99%