Competitive intramolecular cyclizations of epoxides to aromatic and double bond positions

Taylor, Stephen K.; Bischoff, David S.; Blankespoor, Curtis L.; Deck, Paul A.; Harvey, Suzanne M.; Johnson, Patricia; Marolewski, Ariane E.; Mork, Steven W.; Motry, Douglas H.; Eenenaam, Ronald Van

doi:10.1021/jo00300a046

Cited by 11 publications

(9 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Compound 3 (Table ) underwent exclusively double bond cyclization . Compound 16 is similar to 3 , but it has a CH 3 O activating group added to it.…”

Section: Resultsmentioning

confidence: 99%

“…The epoxides used in this study were synthesized by the Wittig and epoxidation procedures developed earlier, as shown in eqs 5 and 6. The aryl dienes used to make epoxides 16 and 21 gave >90% internal epoxidation products.…”

Section: Resultsmentioning

confidence: 99%

“…Biomimetic cyclizations of epoxides, especially epoxy-ene cyclizations, have been investigated for some time − these reactions have already been used to make important natural and medicinal products in high yields. ,, …”

Section: Introductionmentioning

confidence: 99%

“…In previous studies comparing these two related areas of chemistry, we determined the relative facility of epoxide cyclizations to intramolecular aromatic and double bond positions (Table ). When an exo versus endo cyclization can competitively occur, be it aromatic versus double bond or vice versa, the exo process predominates. When both aromatic and double bond cyclization pathways are endo , the aromatic cyclization process occurrs ( 1 → 2 ).…”

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Substituent Effects On Intramolecular Epoxide Cyclizations That Can Competitively Occur at Aromatic or Double Bond Positions¹

1996

Self Cite

View full text Add to dashboard Cite

The effects of substituents on epoxides that can competitively cyclize at either a double bond or aromatic position were determined. Adding a group that would stabilize the transition state of the double bond cyclization of an epoxide that underwent predominantly aromatic cyclization increased the relative amount of the former pathway, but not dramatically. Adding a strong activating substituent to the aromatic group of an epoxide that underwent predominantly double bond cyclization increased the relative amount of aromatic cyclization, but a complex product mixture was obtained. An explanation of the behavior observed is presented.

show abstract

“…Compound 3 (Table ) underwent exclusively double bond cyclization . Compound 16 is similar to 3 , but it has a CH 3 O activating group added to it.…”

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Substituent Effects On Intramolecular Epoxide Cyclizations That Can Competitively Occur at Aromatic or Double Bond Positions¹

1996

Self Cite

View full text Add to dashboard Cite

show abstract

“…Taylor et al [47,48] [50]. Following an analogous procedure, a series of disubstituted oxepanes was synthesized [51].…”

Section: Methodsmentioning

confidence: 99%

Transformation of oxiranes into other oxygen-containing heterocyclic systems

2004

View full text Add to dashboard Cite

The review analyzes published data on the transformations of epoxy derivatives into other oxygencontaining heterocyclic systems, such as cyclic ethers (including cage-like structures), dioxolanes, ortho esters, lactones, and cyclic carbonates, some of which occur in the nature and exhibit biological activity. Reaction mechanisms involving heterolytic, homolytic, enzymatic, and single-electron transfer processes, as well as [2+2]-and [3+3]-cycloadditions, are discussed.

show abstract

Cyclialkylation of Arylalkyl Epoxides with Solid Acid Catalysts

Elings

Downing

Sheldon³

1999

Eur. J. Org. Chem.

View full text Add to dashboard Cite

Solid acids, such as zeolites and clays, catalyse the intramolecular hydroxyalkylation (cyclialkylation) of several arylalkyl epoxides in moderate to excellent conversions and selectivities. The use of solid acids in these cyclialkylations provides a cleaner, better alternative to conventional Lewis and Brønsted acids, enabling a more facile workup of reaction mixtures and, in several cases, better selectivities.

show abstract

Competitive intramolecular cyclizations of epoxides to aromatic and double bond positions

Cited by 11 publications

References 0 publications

Substituent Effects On Intramolecular Epoxide Cyclizations That Can Competitively Occur at Aromatic or Double Bond Positions¹

Substituent Effects On Intramolecular Epoxide Cyclizations That Can Competitively Occur at Aromatic or Double Bond Positions¹

Transformation of oxiranes into other oxygen-containing heterocyclic systems

Cyclialkylation of Arylalkyl Epoxides with Solid Acid Catalysts

Contact Info

Product

Resources

About

Competitive intramolecular cyclizations of epoxides to aromatic and double bond positions

Cited by 11 publications

References 0 publications

Substituent Effects On Intramolecular Epoxide Cyclizations That Can Competitively Occur at Aromatic or Double Bond Positions1

Substituent Effects On Intramolecular Epoxide Cyclizations That Can Competitively Occur at Aromatic or Double Bond Positions1

Transformation of oxiranes into other oxygen-containing heterocyclic systems

Cyclialkylation of Arylalkyl Epoxides with Solid Acid Catalysts

Contact Info

Product

Resources

About

Substituent Effects On Intramolecular Epoxide Cyclizations That Can Competitively Occur at Aromatic or Double Bond Positions¹

Substituent Effects On Intramolecular Epoxide Cyclizations That Can Competitively Occur at Aromatic or Double Bond Positions¹