Synthesis and dynamic behaviour of 1-(dipropylboryl)cyclohepta-2,4-diene

Gridnev, Ilya D.; Gurskii, M. E.; Geiderikh, A. V.; Bubnov, Yurii N.

doi:10.1070/mc1996v006n05abeh000637

Cited by 6 publications

(3 citation statements)

References 15 publications

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“…This mixture of acyclic anions evolves to a 2:3 mixture of cyclic cycloheptadienyl anions 37 and 38. The same mixture of cycloheptadienyl anions is obtained by deprotonation of either 2-methylcyclohepta-1,3diene 24 or 5-methylcyclohepta-1,3-diene (39), suggesting that it represents the thermodynamic equilibrium position.…”

Section: Scheme 4 Study Of the Electrocyclization Of The Heptatrienyl...mentioning

confidence: 75%

“…In 1996, Bubnov and co-workers reported the synthesis and dynamic behavior of 1-(dipropylboryl)cyclohepta-2,4-diene ( 90 ). 39 Deprotonation of trans -hepta-1,3,6-triene ( 40a ) with n -BuLi in THF at –78 °C and warming to –40 °C provided lithium cycloheptadienide 42a , which gave the desired borylated cycloheptadiene in 40% yield (Scheme 13 ).…”

Section: Recent Developments (1996–2023)mentioning

confidence: 99%

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The Electrocyclization of Heptatrienyl Anions

Orellana,

Komijani

2023

Synthesis

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The thermal electrocyclization of heptatrienyl anions is reviewed. We begin with a succinct background on the importance of cycloheptane rings in complex molecules and a brief survey of approaches to their synthesis. We also review the fundamental aspects of this electrocyclization manifold, relying on the Woodward–Hoffmann rules for pericyclic chemistry. Then we survey the literature, covering the burst of discovery in the late 1960s and early 1970s, and the more sporadic reports in from the 1990s to the present day.1 Introduction2 The Electrocyclization of Heptatrienyl Anions3 Discovery and Early Development (1964–1975)4 Recent Developments (1996–2023)5 Concluding Remarks

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Section: Scheme 4 Study Of the Electrocyclization Of The Heptatrienyl...mentioning

confidence: 75%

Section: Recent Developments (1996–2023)mentioning

confidence: 99%

The Electrocyclization of Heptatrienyl Anions

Orellana,

Komijani

2023

Synthesis

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“…Following the first report of an all-carbon anionic 8π electrocyclization reaction to form cycloheptadienes by Kleinschmidt et al in 1968 (Fig. 3), 41 a number of related reactions were published; 42 however, such studies remain rare.…”

Section: Construction Of Seven-membered Carbon Ringsmentioning

confidence: 99%

Recent advances in 8π electrocyclization reactions

Liu

2023

Chem. Commun.

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ChemInform Abstract: Synthesis and Dynamic Behavior of 1‐(Dipropylboryl)cyclohepta‐2,4‐ diene.

et al. 1997

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1997organo-boron compounds, isocyclic C derivatives organo-boron compounds, isocyclic C derivatives S 0044 -160Synthesis and Dynamic Behavior of 1-(Dipropylboryl)cyclohepta-2,4diene. -The title cycloheptadiene (III), prepared by reaction of lithium cycloheptadienide with dipropylborane (II), undergoes two sequential ( 1,3)boron shifts at higher temperatures. As known for other allylboranes, compound (III) reacts with acetone under (1,3) sigmatropic shift to give the non-conjugated dienic alcohol (V). -(GRIDNEV, I. D.; GURSKII, M. E.; GEIDERIKH, A.

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Synthesis and dynamic behaviour of 1-(dipropylboryl)cyclohepta-2,4-diene

Cited by 6 publications

References 15 publications

The Electrocyclization of Heptatrienyl Anions

The Electrocyclization of Heptatrienyl Anions

Recent advances in 8π electrocyclization reactions

ChemInform Abstract: Synthesis and Dynamic Behavior of 1‐(Dipropylboryl)cyclohepta‐2,4‐ diene.

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