Barton Decarboxylation of Cubane-1,4-dicarboxylic Acid: Optimized Procedures for Cubanecarboxylic Acid and Cubane

Eaton, Philip E.; Nordari, N.; Tsanaktsidis, John; Upadhyaya, S. P.

doi:10.1055/s-1995-3961

Cited by 44 publications

(30 citation statements)

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“…Diethyl-adamantane-1,3-dicarboxylate (1) was synthesized by esterification of 1,3-adamantanedicarboxylic acid. Compound 2 was prepared by mono-saponification of the di-esters 1 in the presence of NaOH as the base, according to literature procedures of Eaton [24] and Hussainy [25,26]. Then treatment of compound 2 with five equivalents of thionyl chloride in refluxing THF offered the adamantanecarbonyl chloride (3).…”

Section: Chemistrymentioning

confidence: 99%

Synthesis, crystal structure, superoxide scavenging activity, anticancer and docking studies of novel adamantyl nitroxide derivatives

Zhu

Sun

Wang

et al. 2016

Journal of Molecular Structure

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Section: Chemistrymentioning

confidence: 99%

Synthesis, crystal structure, superoxide scavenging activity, anticancer and docking studies of novel adamantyl nitroxide derivatives

Zhu

Sun

Wang

et al. 2016

Journal of Molecular Structure

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“…A number of syntheses of the highly strained hydrocarbon cubane have been reported, [96] but the shortest so far is that of Australian-born Rowland Pettit-who apparently managed to obtain two Ph.D. degrees-and co-workers at the University of Texas in Austin, who required just six steps from the known 2,5-dibromobenzoquinone 131 (Scheme 29). [88a] The route began with the Diels-Alder reaction between dibromoquinone 131 and cyclobutadieneirontricarbonyl (132), [97] a stable surrogate for the highly reactive cyclobutadiene, in the presence of CAN.…”

Section: Cubane (Pettit 1966)mentioning

confidence: 99%

Quinones as Dienophiles in the Diels–Alder Reaction: History and Applications in Total Synthesis

2014

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In the canon of reactions available to the organic chemist engaged in total synthesis, the Diels–Alder reaction is among the most powerful and well understood. Its ability to rapidly generate molecular complexity through the simultaneous formation of two carboncarbon bonds is almost unrivalled, and this is reflected in the great number of reported applications of this reaction. Historically, the use of quinones as dienophiles is highly significant, being the very first example investigated by Diels and Alder. Herein, we review the application of the Diels–Alder reaction of quinones in the total synthesis of natural products. The highlighted examples span some 60 years from the landmark syntheses of morphine (1952) and reserpine (1956) by Gates and Woodward, respectively, through to the present day examples, such as the tetracyclines.

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“…Unexpectedly, cubane proved to be quite stable, with no decomposition until heated to over 200 °C . Cubane can be prepared in gram quantities by decarboxylation of cubane‐1,4‐dicarboylic acid, which is commercially available . Almost any substituted cubane can be made .…”

Section: Introductionmentioning

confidence: 99%

The Bent Bonds of Cubane

2017

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The carbon–carbon bonding in cubane is shown not to be along the C–C vectors between carbon atoms at the corners of a cube. Instead, the bonding is “bent” as seen in a new single‐crystal X‐ray structure of cubane at 93 K. The bent bond angles and lengths are compared with the geometric angles and with predictions. The distortions from the tetrahedral angle of the sp3‐hybridized carbon atoms are shown to be relatively small in cubane, unlike those in cyclopropane, which are large. Despite this and other differences, cubane and cyclopropane have similar reactivity, a fact that has not been widely recognized. It is suggested that cubane might mimic the chemistry of the cyclopropane ring in the pharmacology of some cyclopropane‐containing drugs.

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Barton Decarboxylation of Cubane-1,4-dicarboxylic Acid: Optimized Procedures for Cubanecarboxylic Acid and Cubane

Cited by 44 publications

References 0 publications

Synthesis, crystal structure, superoxide scavenging activity, anticancer and docking studies of novel adamantyl nitroxide derivatives

Synthesis, crystal structure, superoxide scavenging activity, anticancer and docking studies of novel adamantyl nitroxide derivatives

Quinones as Dienophiles in the Diels–Alder Reaction: History and Applications in Total Synthesis

The Bent Bonds of Cubane

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