Synthesis of heterocycles by radical cyclisation

Bowman, W. Russell; Bridge, Colin F.; Brookes, P. R.

doi:10.1039/a808141g

Cited by 106 publications

(33 citation statements)

References 111 publications

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“…In fact the m=z value is used by chemists on a regular basis to determine the molecular weight of a compound to four decimal places. This method of determining molecular weight is accepted in peer reviewed scientific journals and used as proof of structure [25,26]. In Figs.…”

Section: Article In Pressmentioning

confidence: 99%

A chemist's view of J.M. Calo's comments on: “A new gaseous and combustible form of water” by R.M. Santilli (Int. J. Hydrogen Energy 2006:31(9), 1113–1128)

Cloonan

2008

International Journal of Hydrogen Energy

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Section: Article In Pressmentioning

confidence: 99%

A chemist's view of J.M. Calo's comments on: “A new gaseous and combustible form of water” by R.M. Santilli (Int. J. Hydrogen Energy 2006:31(9), 1113–1128)

Cloonan

2008

International Journal of Hydrogen Energy

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“…Baldwin's rules give helpful guidance as to allowed and disfavored cyclization modes 6, 8. The chain may contain many types of heteroatoms and be configured in many different ways 9–11…”

Section: Introductionmentioning

confidence: 99%

Programming Organic Molecules: Design and Management of Organic Syntheses through Free-Radical Cascade Processes

McCarroll

Walton

2001

Angew. Chem. Int. Ed.

233

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Cascade, domino, or tandem processes, that link together two or more transformations in one pot, are increasing in popularity because they lead to improvements in synthetic efficiency and decreases in environmental impact. Not only do these cascades contain choice mechanistic gems but they also deliver compact and elegant syntheses of complex natural products. Longer cascades require more functional groups precisely configured within carefully designed initial molecular architectures. Such “purposeful” molecules can be thought of as chemical algorithms.This article surveys the phenomenal range of unimolecular free‐radical cascades. A convenient system for classifying free‐radical cascades is described that is useful for evaluating and comparing cascades and aids the design of synthetic routes to polycyclic structures.Double cyclization cascades lead to cyclopentylcyclopentane or bicyclo[3.3.0]octane derivatives. Precursors that contain a ring as a template have been used to control stereochemistry in syntheses of triquinanes and many related compounds. Of the cascades containing ring‐cleavage steps, the most useful are the ring expansions which have opened up new synthetic routes to medium ring polycycles.The key design features of three‐stage unimolecular free‐radical cascades that yielded steroid structures, are linear arrays of radical acceptor units associated with methyl groups distributed every fifth C‐atom in the precursor polyenes. Ring cleavage is the reverse of cyclization. In special, symmetrical structures, therefore, this led to sequences that were reversible, thus launching endlessly repeating cascades supported by delightfully fluxional structures. The science of “programming” organic molecules to achieve particular target structures is maturing rapidly. Coordination and classification of the welter of information in this area is intended to facilitate design and hence to extend the range and complexity of attainable structures.

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“…In addition to simple vinyl iodides (e.g., 4b , R 1 = Me, R 2 = H, R 3 = H), [18] a ( Z )-styrenyl iodide (i.e., 4c , R 1 = Me, R 2 = H, R 3 = Ph) [19] furnished vinyl ether 5c in high yield and without loss of olefin stereochemical fidelity. Aminocyclohexanols bearing isopropyl and allyl substituents on nitrogen afforded the corresponding products in reduced yields ( 5d and 5e ).…”

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confidence: 99%

Nickel‐Catalyzed Intramolecular C−O Bond Formation: Synthesis of Cyclic Enol Ethers

2016

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An efficient and exceptionally mild intramolecular nickel-catalyzed carbon–oxygen bond-forming reaction between vinyl halides and primary, secondary, and tertiary alcohols has been achieved. Zinc powder was found to be an essential additive for obtaining high catalyst turnover and yields. This operationally simple method allows direct access to cyclic vinyl ethers in high yields in a single step.

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Synthesis of heterocycles by radical cyclisation

Cited by 106 publications

References 111 publications

A chemist's view of J.M. Calo's comments on: “A new gaseous and combustible form of water” by R.M. Santilli (Int. J. Hydrogen Energy 2006:31(9), 1113–1128)

A chemist's view of J.M. Calo's comments on: “A new gaseous and combustible form of water” by R.M. Santilli (Int. J. Hydrogen Energy 2006:31(9), 1113–1128)

Programming Organic Molecules: Design and Management of Organic Syntheses through Free-Radical Cascade Processes

Nickel‐Catalyzed Intramolecular C−O Bond Formation: Synthesis of Cyclic Enol Ethers

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