Mechanisms of photochemical reactions in solution. LIII. Cycloaddition of carbonyl compounds to allenes

Gotthardt, Hans; Steinmetz, Reinhard; Hammond, George S.

doi:10.1021/jo01271a035

Cited by 59 publications

(12 citation statements)

References 6 publications

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“…Low yields were obtained and the major product of these reactions tended to be the bis-spirocyclic oxetanes (1,6-dioxaspiro[3.3]heptanes). Around the same time, Hammond and co-workers , extended the Paternò–Büchi reaction with allenes and carbonyl compounds to include xanthone and benzaldehyde (Scheme a). The yields of the product oxetanes were higher, presumably due to the oxetane derivatives being more stable, but bis-spirocyclic oxetanes were also isolated.…”

Section: Synthesis and Reactivity Of 2-methyleneoxetanesmentioning

confidence: 99%

“…The yields of the product oxetanes were higher, presumably due to the oxetane derivatives being more stable, but bis-spirocyclic oxetanes were also isolated. The use of fluorenone also afforded 2-methyleneoxetane 265 ; however, this was always isolated with the isomeric ketone 266 formed as a result of a rearrangement aided by the similar excitation energy of fluorenone and 2-methyleneoxetane 265 (Scheme b). , …”

Section: Synthesis and Reactivity Of 2-methyleneoxetanesmentioning

confidence: 99%

“…The use of fluorenone also afforded 2methyleneoxetane 265; however, this was always isolated with the isomeric ketone 266 formed as a result of a rearrangement aided by the similar excitation energy of fluorenone and 2methyleneoxetane 265 (Scheme 108b). 451,452 In the 1970s, Hudrlik et al 453,454 prepared the parent 2methyleneoxetane 270 through a retro-Diels−Alder reaction (Scheme 109). A lengthy synthesis commenced with a Diels− Alder reaction between anthracene and α-acetoxyacrylonitrile to afford 267, followed by several transformations to afford diol 268.…”

Section: Chemical Reviewsmentioning

confidence: 99%

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Oxetanes: Recent Advances in Synthesis, Reactivity, and Medicinal Chemistry

et al. 2016

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The four-membered oxetane ring has been increasingly exploited for its contrasting behaviors: its influence on physicochemical properties as a stable motif in medicinal chemistry and its propensity to undergo ring-opening reactions as a synthetic intermediate. These applications have driven numerous studies into the synthesis of new oxetane derivatives. This review takes an overview of the literature for the synthesis of oxetane derivatives, concentrating on advances in the last five years up to the end of 2015. These methods are clustered by strategies for preparation of the ring and further derivatization of preformed oxetane-containing building blocks. Examples of the use of oxetanes in medicinal chemistry are reported, including a collation of oxetane derivatives appearing in recent patents for medicinal chemistry applications. Finally, examples of oxetane derivatives in ring-opening and ring-expansion reactions are described.

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Section: Synthesis and Reactivity Of 2-methyleneoxetanesmentioning

confidence: 99%

Section: Synthesis and Reactivity Of 2-methyleneoxetanesmentioning

confidence: 99%

Section: Chemical Reviewsmentioning

confidence: 99%

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Oxetanes: Recent Advances in Synthesis, Reactivity, and Medicinal Chemistry

et al. 2016

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“…The Paternò-Büchi reaction can also be applied to other unsaturated systems other than alkenes, such as dienes [10], allenes [236], acetylenes [237], and ketenimines [236]. When tetramethylallene reacted with aromatic ketones the main products resulted from bis-addition of the carbonyl compounds to give dioxaspiroheptanes [238,239]. On the contrary, 1,1-dimethylallene gave only the monoaddition 2:1 mixture of the adducts in a reaction with aliphatic aldehydes [240].…”

Section: Other Intermolecular Reactionsmentioning

confidence: 99%

Oxetane Synthesis through the Paternò-Büchi Reaction

D’Auria

Racioppi

2013

Molecules

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Abstract:The Paternò-Büchi reaction is a photochemical reaction between a carbonyl compound and an alkene to give the corresponding oxetane. In this review the mechanism of the reaction is discussed. On this basis the described use in the reaction with electron rich alkenes (enolethers, enol esters, enol silyl ethers, enanines, heterocyclic compounds has been reported. The stereochemical behavior of the reaction is particularly stressed. We pointed out the reported applications of this reaction to the synthesis of naturally occuring compounds.

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“…Les spectres infrarouge, de r6sonance magn6tique nucl6aire du proton et du carbone 13C de ces alcools pr6sentent les caract6ristiques habituelles du motif m6thyl6ne cyclobutanique (Skattebol & Solomon, 1965;Gotthardt, Steinmetz & Hammond, 1968;Matsumoto et al, 1971). Ces donn~es etnos r~sultats ant6rieurs sur ce type de condensation (Caub6re & Brunet, 1972) nous permettent de d6finir le squelette 28 carbon6 g6n6ral de deux tricyclo [7,5,0,0 ' ]t6trad6c6ne-7 ols-1 (Fig.…”

Section: Introductionunclassified

Structure cristalline du (1RS,2SR,9SR) tricyclo[7,5,0,0^2,8]tétradécène-7 ol-1

Courtois¹,

Protas²,

Fixari³

et al. 1975

Acta Crystallogr Sect B

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The crystal structure of (1RS, 2SR, 9SR)-tricyclo [7,5,0,02'a]tetradeca-7-en-l-ol has been determined by the symbolic addition procedure. The crystals are monoclinic, space group C2/c, with eight molecules in a cell of dimensions a= 16.88, b= 12.36, c= 25.92 A and fl= 111°50 '. Least-squares refinement with anisotropic temperature factors yielded the final R value of 0.076. The molecules form tetramers through hydrogen bonds in which each oxygen atom is linked to two other oxygens.

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Mechanisms of photochemical reactions in solution. LIII. Cycloaddition of carbonyl compounds to allenes

Cited by 59 publications

References 6 publications

Oxetanes: Recent Advances in Synthesis, Reactivity, and Medicinal Chemistry

Oxetanes: Recent Advances in Synthesis, Reactivity, and Medicinal Chemistry

Oxetane Synthesis through the Paternò-Büchi Reaction

Structure cristalline du (1RS,2SR,9SR) tricyclo[7,5,0,0^2,8]tétradécène-7 ol-1

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Mechanisms of photochemical reactions in solution. LIII. Cycloaddition of carbonyl compounds to allenes

Cited by 59 publications

References 6 publications

Oxetanes: Recent Advances in Synthesis, Reactivity, and Medicinal Chemistry

Oxetanes: Recent Advances in Synthesis, Reactivity, and Medicinal Chemistry

Oxetane Synthesis through the Paternò-Büchi Reaction

Structure cristalline du (1RS,2SR,9SR) tricyclo[7,5,0,02,8]tétradécène-7 ol-1

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Structure cristalline du (1RS,2SR,9SR) tricyclo[7,5,0,0^2,8]tétradécène-7 ol-1