Substituent effect on regioselectivity in the di-π-methane rearrangement: synthesis of disubstituted benzobarrelene derivatives and their photochemistry

Ünaldi, Nermin S.; Balcı, Metin

doi:10.1016/s0040-4039(01)01770-1

Cited by 8 publications

(2 citation statements)

References 19 publications

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“…47 A dicyano derivative (65) was transformed into the di-p-methane isomerization products 66 and 67 (Scheme 14). 48 The reaction was performed in acetone as solvent and triplet sensitizer. Only minor amounts of the corresponding benzocyclooctatetraene derivative 68 were obtained.…”

Section: Reaction Centers Arranged In An Acyclic Systemmentioning

confidence: 99%

5.06 Di-π-methane, Oxa-di-π-methane, and Aza-di-π-methane Photoisomerization

Riguet¹,

Hoffmann²

2014

Comprehensive Organic Synthesis II

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Section: Reaction Centers Arranged In An Acyclic Systemmentioning

confidence: 99%

5.06 Di-π-methane, Oxa-di-π-methane, and Aza-di-π-methane Photoisomerization

Riguet¹,

Hoffmann²

2014

Comprehensive Organic Synthesis II

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“…C 12 H 8 (CN) 2 Valence Isomers. Analogously to Scheme 1, dibromobenzobarrelene 16, made from the dehydrobromination of higher brominated barrelenes such as tetrabromo-1,4ethanonaphthalene, 9 reacts with CuCN to form the dinitrile 17, which is then photolyzed with 254 nm radiation to produce a mixture of 11, 12, and 18 (82, 6, and 12%, respectively), 9,80 which were separated by column chromatography (Scheme 3).…”

Section: ■ Introductionmentioning

confidence: 99%

Accurate Crystal Structures of C₁₂H₉CN, C₁₂H₈(CN)₂, and C₁₆H₁₁CN Valence Isomers Using Nonspherical Atomic Scattering Factors

et al. 2022

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Fourteen crystal structures, mostly from good-quality datasets but including some marginal and twinned exemplars, from a series of novel polycyclic benzo- and naphtho-fused organic nitriles are presented and accurately described, including some related structures of a bromo-substituted and partially hydrogenated analogues. These structures represent a considerable increase in the number of published structures within their archetypes. This work highlights the significant advancement in structural refinement software proffered by NoSpherA2, which enables Hirshfeld Atom Refinement (HAR) of the structures within Olex2 v1.5. This results in the determination of C–H bond lengths with near to neutron diffraction accuracies at far lower experimental cost, and with an average improvement in C–C bond precision of 42% compared to Independent Atom Model refinements. H-atoms (apart from disordered components) refined well with anisotropic displacement parameters. Nonclassical H-bonding (C–H···NC) in this series is analyzed, and dipolar nitrile–nitrile interactions (CN···CN) in three major motifs described by (WoodP. A. Wood, P. A. Acta Cryst. B200864393396) are found in 9 out of 13 nitrile-containing compounds of this series, a much higher proportion than the global average of 21% of nitrile-containing compounds. The HAR/NoSpherA2 approach shows increasing benefits with better data quality without apparent discontinuities.

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Di‐Π‐Methane Rearrangement

2010

Comprehensive Organic Name Reactions and Reagents

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This reaction, known as the Zimmerman rearrangement, di‐π‐methane rearrangement, di‐π‐methane photorearrangement, or di‐π‐methane reaction, is a photochemical reaction of a molecular entity comprising two π‐systems separated by a saturated carbon atom (a sp 3 carbon, e.g. a methylene group) involving the migration of one π‐moiety bonded to the saturated carbon to other π‐moiety accompanied by the concomitant formation of a cyclopropane ring from the remaining π‐moiety and methylene group. This rearrangement has been reported to consist at least six versions and all these variants differ from each other. This rearrangement has high regiospecificity with a strong preference for migration of the less conjugated π‐moiety to the more conjugated one. This rearrangement has proven valuable in preparation of substituted cyclopropanes.

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Substituent effect on regioselectivity in the di-π-methane rearrangement: synthesis of disubstituted benzobarrelene derivatives and their photochemistry

Cited by 8 publications

References 19 publications

5.06 Di-π-methane, Oxa-di-π-methane, and Aza-di-π-methane Photoisomerization

5.06 Di-π-methane, Oxa-di-π-methane, and Aza-di-π-methane Photoisomerization

Accurate Crystal Structures of C₁₂H₉CN, C₁₂H₈(CN)₂, and C₁₆H₁₁CN Valence Isomers Using Nonspherical Atomic Scattering Factors

Di‐Π‐Methane Rearrangement

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Substituent effect on regioselectivity in the di-π-methane rearrangement: synthesis of disubstituted benzobarrelene derivatives and their photochemistry

Cited by 8 publications

References 19 publications

5.06 Di-π-methane, Oxa-di-π-methane, and Aza-di-π-methane Photoisomerization

5.06 Di-π-methane, Oxa-di-π-methane, and Aza-di-π-methane Photoisomerization

Accurate Crystal Structures of C12H9CN, C12H8(CN)2, and C16H11CN Valence Isomers Using Nonspherical Atomic Scattering Factors

Di‐Π‐Methane Rearrangement

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Accurate Crystal Structures of C₁₂H₉CN, C₁₂H₈(CN)₂, and C₁₆H₁₁CN Valence Isomers Using Nonspherical Atomic Scattering Factors