Conjugative and homoconjugative effects in 2-heterobicyclo[3.2.1]octa-3,6-dienes

Barraclough, P.; Bilgiç, Sevim; Pedley, J. B.; Rogers, Antony J.; Young, Douglas W.

doi:10.1016/0040-4020(79)85014-0

Cited by 8 publications

(3 citation statements)

References 39 publications

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“…Although the PE spectra of a variety of 2-heterobicyclo-[3.2.l]octa-3,6-dienes, 38, give evidence of conjugative and homoconjugative effects, there is no indication of any special neutral bis-homoaromatic stabilization (128). In another study, the unique symmetry characteristics of 39 enabled Brown to obtain experimental corroboration of the assumed 0.8-eV inductive stabilization afforded by an allylic oxygen (129).…”

mentioning

confidence: 98%

Electron spectroscopy: ultraviolet and x-ray excitation

Baker¹,

Brisk²,

Liotta³

1980

Anal. Chem.

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mentioning

confidence: 98%

Electron spectroscopy: ultraviolet and x-ray excitation

Baker¹,

Brisk²,

Liotta³

1980

Anal. Chem.

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“…The two olefins of diene 1 [6][7][8] can each be differentiated chemoselectively ( Figure 1). Reaction sequences that require electron-deficient alkenes happen readily at the C6-C7 olefin, whereas reactions requiring electron-rich alkenes occur readily at the C3-C4 olefin.…”

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confidence: 99%

Development of a Method for the Synthesis of 4-Aryl-Functionalized 2-Azabicyclo[3.2.1]octanes

Armstrong

Bergmeier

2017

Synthesis

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A method for the synthesis of 4-substituted azabicyclo[3.2.1]octanes from N-tosyl-2-azabicyclo[3.2.1]octa-3,6-diene, a versatile bicyclic heterocycle not commonly used in medicinal chemistry research, is presented. The method uses bromination, followed by Suzuki coupling, and subsequent reduction and deprotection. The desired 4-substituted azabicyclo[3.2.1]octanes were obtained in moderate to high yields.

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“…Few examples of such modifications have been reported. These modifications are largely limited to the reduction of one or both double bonds,9–11 dihyroxylation of the 6,7-olefin12 and cycloaddition reactions with the 6,7-olefin 13,14…”

mentioning

confidence: 99%

Ring expansion of substituted norbornadienes for the synthesis of mono- and disubstituted 2-azabicyclo[3.2.1]octadienes

Emelda

Bergmeier

2008

Tetrahedron Letters

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We have studied the conversion of substituted norbornadienes into a substituted 2-azabicyclo[3.2.1]octadiene system via reaction with toluenesulfonyl azide. We have found that both and mono- and disubstituted norbornadienes will undergo the cycloaddition/rearrangement sequence to provide the bicyclooctadiene ring system as a single regioisomer. The 2-azabicyclo[3.2.1]octane ring system can be prepared from the unsaturated 2-azabicyclo[3.2.1]octadiene ring system.

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Conjugative and homoconjugative effects in 2-heterobicyclo[3.2.1]octa-3,6-dienes

Cited by 8 publications

References 39 publications

Electron spectroscopy: ultraviolet and x-ray excitation

Electron spectroscopy: ultraviolet and x-ray excitation

Development of a Method for the Synthesis of 4-Aryl-Functionalized 2-Azabicyclo[3.2.1]octanes

Ring expansion of substituted norbornadienes for the synthesis of mono- and disubstituted 2-azabicyclo[3.2.1]octadienes

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