On the planarity of the cyclobutane ring in the crystal of dimethyl 2,4-bis(3,4-dimethoxyphenyl)cyclobutane-1,3-dicarboxylate: a natural bond orbital and Hirshfeld surface analysis study

The α-form of this 1,3-di-(substituted)-2,4-bis-(substituted)-cyclobutane derivative displays a planar ring in the gas phase and solution. The intermolecular interactions in the crystal have been determined.

Photochemically Induced Solid State Dimerisation of Resveratrol Analogues: A Greener Synthetic Process

The photochemical dimerisation of resveratrol analogues in the solid state to generate chiral phenyl substituted cyclobutanes is described. NMR spectroscopic and X-ray crystallographic methods have confirmed that the dimerisation leads to the head to tail orientation of the phenyl group substituents in the cyclobutane derivative. Interestingly, the parent compound, resveratrol, in the solid state, did not form a cyclobutane dimer, but the O-acetyl analogues gave the corresponding cyclobutane dimers in high yield, suggesting that the close packing of molecules together with the electron density through the conjugated double bond of the resveratrol structure are important determinants for photodimerisation to occur in the solid state.

A Base-Promoted One-Pot Asymmetric Friedel–Crafts Alkylation/Michael Addition of 4-Substituted Indoles

Herein, we report a base-promoted Zn(II)–bis(oxazoline)-catalyzed one-pot Friedel–Crafts alkylation/Michael addition of 3-(indol-4-yl)acrylonitrile derivatives with trans-β-nitrostyrenes to yield the tricyclic core of the ergoline skeleton in up to 71% yield and 85% ee. During the purification of 3-(indol-4-yl)acrylonitrile, the key substrate for catalytic studies, a novel trans-cis-trans-cyclobutane derivative, thought to be formed via a [2+2] light-promoted cycloaddition, was identified by X-ray crystallographic analysis. Finally, a novel class of 4-substituted bis(indole)methane derivatives were serendipitously prepared in excellent yield by reacting 4-substituted indole derivatives with 4-nitrobenzaldehyde. One bis(indole)methane was characterized by X-ray crystallographic analysis.

The sunlight-driven photosalient effect of a 1D coordination polymer and the release of an elusive cyclobutane derivative

A 1D coordination polymer exhibits photosalient effect due to photochemical [2+2] cycloaddition reaction by UV as well as sunlight irradiation accompanied by the release of free cyclobutane ligand.

The regioselective [2 + 2] photocycloaddition reaction of 2-(3,4-dimethoxystyryl)quinoxaline in solution

The [2+2] photocycloaddition between two molecules of (E)-2-(3,4-dimethoxystyryl)-quinoxaline (1) in an acetonitrile solution is the first example of the regioselective and stereospecific formation of a cyclobutane derivative without applying any method for the preorganization of molecules in a dilute solution.

cis,trans,cis-1,2,3,4-Tetrakis[2-(ethylsulfanyl)phenyl]cyclobutane

The title cyclobutane derivative, C36H40S4, formed serendipitously through a photochemically initiated [2 + 2] cycloaddition. The asymmetric unit contains half a molecule with the 2-(ethylsulfanyl)phenyl substituents in acisconfiguration, the other half of the molecule being generated by the application of a twofold rotation operation. The substituents in both halves of the molecules are in atransarrangement relative to each other. The cyclobutane ring shows angular and torsional strains, with C—C—C bond angles of 89.80 (8) and 88.40 (8)°, and an average absolute torsion angle of 14.28 (10)°. The angle of pucker in the ring is 20.27 (12)°. The Ccb—Ccb—Cbangles between the cyclobutane (cb) ring atoms and the attached benzene (b) ring atoms are widened and range from 115.19 (10) to 121.66 (10)°. A weak intramolecular C—H...S hydrogen-bonding interaction between one of the cyclobutane ring H atoms and the S atom may help to establish the molecular conformation. No specific intermolecular interactions are found.

Photonics of styrylquinoline dyads

Three types of bichromophoric styrylquinoline (SQ) dyads are discussed in the review: bisstyrylquinoline dyads, styrylquinoline-merocyanine dyads, and styrylquinoline-naphthol dyads, in comparison with the corresponding model monochromophoric compounds. A variety of photochemical and photophysical processes is observed in the dyads: photoluminescence, reversible and kinetic-driven one-way photoisomerization, [2+2]photocycloaddition with formation of a single rctt-isomer of the cyclobutane derivative, Forster resonance energy transfer (FRET) where the SQ chromophore can act as an energy donor or acceptor. Operation of the dyads as photoswitches and molecular logic gates is also considered.

Photochemical dimerization of a fluorinated dibenzylideneacetone in chloroform solution

(1E,4E)-1,5-Bis(2,6-difluorophenyl)penta-1,4-dien-3-one, C17H10F4O, (I), dimerizes under sunlight in chloroform solution to form the corresponding cyclobutane derivative, (2E,2′E)-1,1′-[2,4-bis(2,6-difluorophenyl)cyclobutane-1,3-diyl]bis[3-(2,6-difluorophenyl)prop-2-en-1-one], C34H20F8O2, (II). The crystal structure of (I) explains why no topochemical dimerization can occur in the solid state. In the solid, molecules of dimer (II) show the `truxillic acid'-type arrangement of crystallographic centres of inversion, with half a molecule per asymmetric unit and cell dimensions closely related to those of the monomer. Intermolecular interactions in both solids are dominated by C—H...O and C—H...F contacts and also comprise interactions with aromatic systems (C—H...π and π–π).