Woodward-Hoffmann rules: Electrocyclic reactions

Vollmer, John J.; Servis, Kenneth L.

doi:10.1021/ed045p214

Cited by 18 publications

(8 citation statements)

References 25 publications

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“…These [2+2] cyclization reactions would lay the groundwork for novel synthetic routes to overcome activation energy barriers in producing various cyclobutyl derivatives [31], which can be involved in different aspects of medicinal chemistry as well as industrial processes for macrocyclic polymerization. The equation given below represents preliminary research on the ability of this Organo-Re(II) electrocatalyst to induce cyclization reactions of terminal alkenes in creating syn-and antiisomers of cyclobutyl derivatives following Woodward-Hoffman rules [32].…”

Section: Electrochemistry As a Synthetic Toolmentioning

confidence: 99%

Indispensable Applications of Electrochemical Techniques to Organic Synthetic Reactions: Enhancing Versatility and

Dick¹,

Chong²

2012

Organic Chem Curr Res

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which is toxic, causing hyperbilirubinemia and gout [13-15]. For the palladium catalyzed heterolytic CC coupling reactions, the metal center is one of the more expensive rare earth metals [11,12], making olefin metathesis and cross coupling impractical compared to current electrochemical applications presented below. The cost for many CC coupling reactions due to these catalysts comes with a great price: not only is the opportunity cost of time and low yields involved, but health and physiological impediments must be taken into consideration along with the exorbitant expense of the transition metal itself.

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Section: Electrochemistry As a Synthetic Toolmentioning

confidence: 99%

Indispensable Applications of Electrochemical Techniques to Organic Synthetic Reactions: Enhancing Versatility and

Dick¹,

Chong²

2012

Organic Chem Curr Res

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“…The Cope rearrangement, and the Claisen reaction are often cited (20)(21)(22)(23) as examples of pericyclic six electron [3,3] sigmatropic shifts.…”

Section: Aromaticity Rules Tor Pericyclic Transition Statesmentioning

confidence: 99%

Structure-resonance theory for pericyclic transition states

Herndon

1981

J. Chem. Educ.

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“…If more than one pericyciic reaction (26)(27)(28)(29)(30)(31)(32) is possible for a ketene then the stereochemical variable of perispecificity must he studied; i.e., which process is selected by the ketene and what is the quantitative preference for that process. For example, a ketene is allowed by the considerations of orbital symmetry (26) to cycloadd to 1,3-cyclopentadiene (acting as the ketenophile) in either a (ir2 + tt4) or a (ir2 + ?r2) manner.…”

Section: Stereochemical Variables: Some Definitionsmentioning

confidence: 99%