Synthesis of 5-(2-methoxy-1-naphthyl)- and 5-[2-(methoxymethyl)-1-naphthyl]-11<i>H</i>-benzo[<i>b</i>]fluorene as 2,2'-disubstituted 1,1'-binaphthyls via benzannulated enyne–allenes

Wang, Yu-Hsuan; Bailey, Joshua F; Petersen, Jeffrey L.; Wang, Kung K.

doi:10.3762/bjoc.7.58

Cited by 11 publications

(4 citation statements)

References 32 publications

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“…Over many years, dehydro‐Diels‐Alder reactions have received ample attention from the scientific community . Among many variants, the tridehydro‐Diels‐Alder reactions of enyne‐allenes and enyne‐carbodiimides have been of major concern to us due to their interesting mechanistic facets. A close analogue with a comparable degree of unsaturation is the didehydro‐Diels‐Alder (DDDA) reaction of enyne‐ketoenes.…”

Section: Introductionsupporting

confidence: 72%

Dynamic effects in the didehydro‐Diels‐Alder (DDDA) reaction of enyne‐ketoenes: 50% stepwise bond formation in spite of concerted transition state

Rana

Paul

Schmittel

2017

J of Physical Organic Chem

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Section: Introductionsupporting

confidence: 72%

Dynamic effects in the didehydro‐Diels‐Alder (DDDA) reaction of enyne‐ketoenes: 50% stepwise bond formation in spite of concerted transition state

Rana

Paul

Schmittel

2017

J of Physical Organic Chem

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“…148) with potassium tert-butoxide in refluxing toluene. 163 A 1,3-prototropic rearrangement was responsible for the in situ formation of enyneallene 149 which in turn underwent a Schmittel cyclization to generate biradical 150. An intramolecular radical-radical coupling finally afforded the corresponding benzo[b]fluorene derivative 152 upon hydrogen shift occurring in 151.…”

Section: Synthesis Of Naphthalenesmentioning

confidence: 99%

(Hetero)aromatics from dienynes, enediynes and enyne–allenes

et al. 2016

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The construction of aromatic rings has become a key objective for organic chemists. While several strategies have been developed for the functionalization of pre-formed aromatic rings, the direct construction of an aromatic core starting from polyunsaturated systems is yet a less explored field. The potential of such reactions in the formation of aromatics increased at a regular pace in the last few years. Nowadays, there are reliable and well-established procedures to prepare polyenic derivatives, such as dienynes, enediynes, enyne-allenes and hetero-analogues. This has stimulated their use in the development of innovative cycloaromatizations. Different examples have recently emerged, suggesting large potential of this strategy in the preparation of (hetero)aromatics. Accordingly, this review highlights the recent advancements in this field and describes the different conditions exploited to trigger the process, including thermal and photochemical activation, as well as the use of transition metal catalysis and the addition of electrophiles/nucleophiles or radical species.

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“…Various polycylic aromatic compounds, mostly benzofluorenols and cyclobut(a)indenes, were equally synthesized . Wang et al .…”

Section: Factors Influencing the Schmittel (C2–c6) Cyclizationmentioning

confidence: 99%

The thermal C²–C⁶ (Schmittel)/ene cyclization of enyne–allenes – crossing the boundary between classical and nonstatistical kinetics

Schmittel

Vavilala

Çınar

2011

J of Physical Organic Chem

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The thermal C 2 -C 6 /ene cyclization of enyne-allenes has become an exciting venue for both mechanistic and synthetic studies. While at first most efforts were aimed at establishing the diradical nature of the thermal process and to derive therefrom efficient protocols for synthetic schemes, recent evidence has disclosed the C 2 -C 6 cyclization as a unique reaction heavily influenced by nonstatistical dynamic effects. Depending on the substituents at the enyne-allene, one can readily identify transitions between classical and nonstatistical behaviors on the basis of experimental data. We are grateful to him for his friendship and many scientific enlightenments.a M. Schmittel, C. Vavilala, M. E. Cinar FB 8 (

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Synthesis of 5-(2-methoxy-1-naphthyl)- and 5-[2-(methoxymethyl)-1-naphthyl]-11H-benzo[b]fluorene as 2,2'-disubstituted 1,1'-binaphthyls via benzannulated enyne–allenes

Cited by 11 publications

References 32 publications

Dynamic effects in the didehydro‐Diels‐Alder (DDDA) reaction of enyne‐ketoenes: 50% stepwise bond formation in spite of concerted transition state

Dynamic effects in the didehydro‐Diels‐Alder (DDDA) reaction of enyne‐ketoenes: 50% stepwise bond formation in spite of concerted transition state

(Hetero)aromatics from dienynes, enediynes and enyne–allenes

The thermal C²–C⁶ (Schmittel)/ene cyclization of enyne–allenes – crossing the boundary between classical and nonstatistical kinetics

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Synthesis of 5-(2-methoxy-1-naphthyl)- and 5-[2-(methoxymethyl)-1-naphthyl]-11H-benzo[b]fluorene as 2,2'-disubstituted 1,1'-binaphthyls via benzannulated enyne–allenes

Cited by 11 publications

References 32 publications

Dynamic effects in the didehydro‐Diels‐Alder (DDDA) reaction of enyne‐ketoenes: 50% stepwise bond formation in spite of concerted transition state

Dynamic effects in the didehydro‐Diels‐Alder (DDDA) reaction of enyne‐ketoenes: 50% stepwise bond formation in spite of concerted transition state

(Hetero)aromatics from dienynes, enediynes and enyne–allenes

The thermal C2–C6 (Schmittel)/ene cyclization of enyne–allenes – crossing the boundary between classical and nonstatistical kinetics

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The thermal C²–C⁶ (Schmittel)/ene cyclization of enyne–allenes – crossing the boundary between classical and nonstatistical kinetics