A Simple Synthesis of [2.2.2.2]-Paracyclophane-1,9,17,25-tetraene by a Wittig Reaction.

Thulin, Bengt; Wennerström, Olof; Högberg, Hans‐Erik; Smidsrød, O.; Dahl, O.; Buchardt, O.; Schroll, G.

doi:10.3891/acta.chem.scand.29b-0138

Cited by 32 publications

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“…The [2.2.2.2]paracyclophane was prepared by hydrogenation at atmospheric pressure of [2.2.2.2]paracyclophane-1,9,17,25-tetraene according to a literature method . The product was characterized with 1 H NMR and IR spectroscopies and its spectra compared with those of the authentic samples.…”

Section: Methodsmentioning

confidence: 99%

Larger Cyclophanes: Synthesis and Structural Characterization of [2.2.2.2]Paracyclophane Compounds with SbBr₃and BiBr₃

et al. 1998

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Section: Methodsmentioning

confidence: 99%

Larger Cyclophanes: Synthesis and Structural Characterization of [2.2.2.2]Paracyclophane Compounds with SbBr₃and BiBr₃

et al. 1998

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“…By the same token, the reaction of bis(phosphonium) salt 38 with terephthalaldehyde ( 39 ) did not result in the formation of [2.2]paracyclophane‐1,9‐diene ( 40 ). Instead, cyclophanetetraene 41 was obtained in just 15 % yield 33. Larger cyclophanes, for example, 43 34 and 45 ,35 have been synthesized using both one‐ and two‐component approaches (Scheme ), but the yields are typically poor.…”

Section: The Wittig and Related Reactionsmentioning

confidence: 99%

Olefination Reactions in the Synthesis of Cyclophanes

Bodwell

Nandaluru

2012

Israel Journal of Chemistry

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A survey of olefination reactions that have been used in the synthesis of cyclophanes is presented. This covers the Ramberg-Bäcklund reaction, the Wittig and related reactions, the McMurry and related reactions, ring-closing metathesis (alkenes, alkynes and ene-ynes), aldol condensations and Siegrist reactions, as well as miscellaneous reactions. The McMurry reaction and ring-closing metathesis have enjoyed the greatest popularity in recent years, but they are typically used for complementary purposes. In virtually all cases, the McMurry reaction is used to install a twocarbon (1,2-ethenylene) bridge, whereas ring-closing metathesis is used to construct bridges that are at least fourmembered, but usually considerably longer. Some wellknown olefinations have seen little or no use in the field of cyclophane chemistry.The Ramberg-Bäcklund reaction [9] is the final step in a two-to three-step thioether-to-alkene conversion. As such, it appears to be well-suited for the synthesis of alkene-containing cyclophanes. Even though it applies to pre-existing cyclophanes, it warrants attention in the context of this review because both bonds of the newly formed alkene are generated during the reaction. Within the broader scope of organic synthesis, the Ramberg-Bäcklund reaction has been exploited frequently to introduce a double bond into large rings, [10] small rings [11] and more exotic ring systems such as cyclic enediynes. [12] However, it has not performed well in the synthesis of cyclophanes.The first cyclophanes to be synthesized using the Ramberg-Bäcklund reaction were the isomeric biphenylophanes (Z,Z)-7 and (E,E)-7 (Scheme 3). [13] As expected from mechanistic considerations, [14] they were formed stereospecifically in good yield (both 65 %) from the diastereomeric sulfones meso-6 and (AE)-6, respectively. Interestingly, the report of these very good results came shortly after Boekelheide wrote that "the Ramberg-Bäcklund reaction is unsatisfactory when applied to 2,11-dithia-[3.3]cyclophanes". [15] Prior to Boekelheides comment on the Ramberg-Bäcklund reaction, Martel reported that a Ramberg-Prof. Graham Bodwell obtained his B.Sc. and M.Sc. from the University of Victoria, Canada, working with Prof. Reginald Mitchell on cyclophanes. He then moved to Braunschweig, Germany, where he joined the group of Prof. Dr. Henning Hopf as a "Doktorand". Cyclophanes were also the focus of his doctoral research. He then took a break from cyclophanes and worked in the field of asymmetric synthesis as a post-doctoral fellow with Prof. Steve Davies at Oxford University. He then accepted a faculty position at Memorial University, where he now holds the rank of Professor. Cyclophanes have always been one of his core research interests.Penchal Reddy Nandaluru obtained his B.Sc. and M.Sc. from Sri Venkateswara University, India, and then worked as a chemist with AVRA Laboratories in India before joining the group of Prof. Graham Bodwell at Memorial University in St. John's, NL, Canada. The main theme of his doctoral research is the appli...

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“…Cyclophanes 3a and 3b were prepared by the reaction of this salt and terephthalaldehyde. 12 The reaction mixture was extracted with diethyl ether and purified by column chromatography (silica gel, methylene chloride). The first yellow fraction (2-3%) collected was composed of the two isomers.…”

Section: Synthesis Of Cyclophanes 3a and 3bmentioning

confidence: 99%

Substituted [24]paracyclophanes

Shabtai¹,

Frenkiel²,

Cohen³

et al. 1997

J. Chem. Soc., Perkin Trans. 2

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A Simple Synthesis of [2.2.2.2]-Paracyclophane-1,9,17,25-tetraene by a Wittig Reaction.

Cited by 32 publications

References 0 publications

Larger Cyclophanes: Synthesis and Structural Characterization of [2.2.2.2]Paracyclophane Compounds with SbBr₃and BiBr₃

Larger Cyclophanes: Synthesis and Structural Characterization of [2.2.2.2]Paracyclophane Compounds with SbBr₃and BiBr₃

Olefination Reactions in the Synthesis of Cyclophanes

Substituted [24]paracyclophanes

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A Simple Synthesis of [2.2.2.2]-Paracyclophane-1,9,17,25-tetraene by a Wittig Reaction.

Cited by 32 publications

References 0 publications

Larger Cyclophanes: Synthesis and Structural Characterization of [2.2.2.2]Paracyclophane Compounds with SbBr3and BiBr3

Larger Cyclophanes: Synthesis and Structural Characterization of [2.2.2.2]Paracyclophane Compounds with SbBr3and BiBr3

Olefination Reactions in the Synthesis of Cyclophanes

Substituted [24]paracyclophanes

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Larger Cyclophanes: Synthesis and Structural Characterization of [2.2.2.2]Paracyclophane Compounds with SbBr₃and BiBr₃

Larger Cyclophanes: Synthesis and Structural Characterization of [2.2.2.2]Paracyclophane Compounds with SbBr₃and BiBr₃