Photochemical decarbonylation of unsaturated lactones and carbonates

Chapman, O. L.; McIntosh, C. L.

doi:10.1039/c29710000383

Cited by 52 publications

(29 citation statements)

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“…The photochemistry of five-membered heterocyclic a-carbonyl compounds in different solutions was studied by several authors for a long time [2][3][4][5]. Margaretha and co-workers [6][7][8][9][10][11][12][13][14][15][16][17] reported that upon irradiation 2(5H)-thiophenones behave quite differently from the corresponding oxygen-based heterocycles.…”

Section: Introductionmentioning

confidence: 99%

UV-induced unimolecular photochemistry of 2(5H)-furanone and 2(5H)-thiophenone isolated in low temperature inert matrices

Breda

Reva

Fausto

2009

Vibrational Spectroscopy

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Section: Introductionmentioning

confidence: 99%

UV-induced unimolecular photochemistry of 2(5H)-furanone and 2(5H)-thiophenone isolated in low temperature inert matrices

Breda

Reva

Fausto

2009

Vibrational Spectroscopy

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“…ortho ‐Quinone methides are highly reactive intermediates having fleeting existence. ortho ‐Quinone methides were first employed by Fries and Kann in 1907 but only a decade later the direct reality of this intermediate was confirmed by low‐temperature IR spectroscopy . Later Vaisserman and co‐workers exposed its structure from X‐ray diffraction by trapping in an iridium complex .…”

Section: Brief History Of Ortho‐quinone Methides and Its Synthetic Utmentioning

confidence: 99%

Applications of Bifunctional Organocatalysts on ortho‐Quinone Methides

2019

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ortho-Quinone methides are important structures, having a cyclohexadiene core bearing an exocyclic alkylidiene and carbonyl functionality at the ortho-position, and are widely used as essential intermediates in organic synthesis. These reactive intermediates are also used as important building blocks for the construction of a variety of heterocycles by hetero Diels-Alder, electrocyclization reactions. Moreover, ortho-quinone methides are a class of electrophiles, serving as Michael acceptors leading to conjugate additions with various nucleophiles. In general, ortho-Quinone methides have transient existence and are highly reactive in nature. ortho-Quinone methides have been generated in situ from stable precursors using either Brønsted acids or Brønsted bases. In the last few years, ortho-quinone methides have been explored as imperative class of substrates in various bifunctional organocatalysts mediated asymmetric conjugate additions, cycloannulation, acyl-transfer reaction, thiolation and hydrophosphination reactions. This review illustrates recent advancements of asymmetric transformations of ortho-quinone methides with bifunctional H-bonding organocatalysts.[a] S.

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“…The photochemistry of unsaturated γ-lactones such as 2(3H)-and 2(5H)-furanones (see Scheme 1) is well established [1][2][3][4][5][6][7][8]. Depending on structural features and irradiation conditions, such lactones undergo several phototransformations including decarbonylation [1], decarboxylation [9], solvent addition to the double bond [10], migration of aryl substituents [11], and dimerisation [12].…”

Section: Introductionmentioning

confidence: 99%