Electron-transfer photooxygenation of tetraphenylallene formation of 1,3-dihydroperoxy-1, 1,3,3-tetraphenyl-2-propanone and its decomposition under chemiluminescence

Gollnick, Klaus; Schnatterer, Albert

doi:10.1016/s0040-4039(00)61872-5

Cited by 12 publications

(6 citation statements)

References 19 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…An early report showed that the photooxygenation of allenes with 1 O 2 yielded unstable tetraoxaspirocycloheptenes, which underwent decomposition to yield aldehydes or ketones by releasing CO 2 . Reaction of 1,3-di( tert -butyl)allene 320 with m -CPBA in hexane afforded allene monoxide 321 , which may undergo rearrangement upon heating to form trans -2,3-di-( tert -butyl)cyclopropanone 322 (Scheme ) …”

Section: Oxidations or Episulfidationsmentioning

confidence: 99%

Some Typical Advances in the Synthetic Applications of Allenes

2005

Chem. Rev.

1,353

256

View full text Add to dashboard Cite

In 1989, Kakiuchi et al. reported that under irridation propadiene can undergo [2+2]-cycloaddition with R,β-unsaturated cyclohexenones to afford methylene-cyclobutane-containing bicyclic products 1 (Scheme 1). 6 Shi et al. reported that under the catalysis of DABCO, N-tosylated imines 2 can undergo [2+2]cycloaddition with 2,3-butadienoate or 3,4-pentadien-2-one to afford azetidine derivatives 3. 7 The reaction proceeded via the nucleophilic addition of DABCO to the electron-deficient allene forming 4-and 5-type intermediate, which may undergo 1,2-addition with the imines to afford 6. Intramolecular conjugate Scheme 1

show abstract

Section: Oxidations or Episulfidationsmentioning

confidence: 99%

Some Typical Advances in the Synthetic Applications of Allenes

2005

Chem. Rev.

1,353

256

View full text Add to dashboard Cite

show abstract

“…In some of these cases, the reaction mechanism was assumed to proceed via a hydroperoxide intermediate . 2,2,4,4-Tetraphenyloxetan-3-one 201 was also formed by dehydration of 1,3-dihydroxy-1,1,3,3-tetraphenyl-2-propanone with sulfuric acid in acetic acid . The starting product was obtained after reduction of 1,3-dihydroperoxy-1,1,3,3-tetraphenyl-2-propanone, which was formed itself by electron-transfer photooxygenation of tetraphenylallene …”

Section: B2 Oxidation Reactionsmentioning

confidence: 99%

“…140 2,2,4,4-Tetraphenyloxetan-3-one 201 was also formed by dehydration of 1,3-dihydroxy-1,1,3,3-tetraphenyl-2-propanone with sulfuric acid in acetic acid. 141 The starting product was obtained after reduction of 1,3-dihydroperoxy-1,1,3,3-tetraphenyl-2-propanone, which was formed itself by electrontransfer photooxygenation of tetraphenylallene. 141 Another method, analogous to the one applied for the synthesis of azetidin-3-ones (vide supra), involved the lead(IV) acetate oxidation of 2,2,4,4-tetrasubstituted-3-hydroxyoxetane-3-carboxylic acids 205 (Scheme 56).…”

Section: B2 Oxidation Reactionsmentioning

confidence: 99%

The Chemistry of Azetidin-3-ones, Oxetan-3-ones, and Thietan-3-ones

et al. 2001

View full text Add to dashboard Cite

I. Introduction 29 II. The Chemistry of Azetidin-3-ones 29 A. Structural Data 29 B. Synthetic Methods for Azetidin-3-ones 31 B.1. Carbonyl Group Generation in the Azetidine Ring 31 B.2. Intramolecular Cyclization Reactions 34 B.3. 1,3-Dipolar Cycloaddition Reactions 36 C. Chemical Properties of Azetidin-3-ones 37 C.1. Transformations of the Carbonyl Group 37 C.2. Condensation Reactions − Synthesis of 2-Benzylideneazetidin-3-ones 40 C.3. Ring Transformations of Azetidin-3-ones 40 C.4. Miscellaneous 41 III. The Chemistry of Oxetan-3-ones 42 A. Structural Data 42 B. Synthetic Methods for Oxetan-3-ones 43 B.1. Decomposition of Diazoketones 43 B.2. Oxidation Reactions 44 B.3. Intramolecular Displacement Reactions 46 B.4. Miscellaneous 47 C. Chemical Properties of Oxetan-3-ones 48 C.1. Ring Opening and Ring Expansion of Oxetan-3-ones 48 C.2. Transformations of the Carbonyl Group 49 IV. The Chemistry of Thietan-3-ones 50 A. Synthetic Methods for Thietan-3-ones 51 A.1. Synthesis from Acyclic Precursors 51 A.2. Synthesis by Ring Transformations 53 B. Chemical Properties of Thietan-3-ones 54 B.1. Transformations of the Carbonyl Group 55 B.2. Aldol Reactions 56 B.3. Ring Transformations 56 V. Acknowledgments 58 VI. References 58

show abstract

“…On this ground, DCA was found a suitable sensitizer to induce the photooxygenation of a great variety of organic compounds such as alkenes [84,[94][95][96][97][98], alkynes [99,100], sulfides [84,98,101], dienes [84], sulfoxides [102], cycloalkanes [103,104], cycloalkenes [105,106], epoxides [107,108], aziridines [109], allenes [110], dioxenes [111], p-dioxins [111,112], aromatic substrates [113], tertiary amines [114], and of great interest from the mechanistic point of view, sterically hindered olefines [97,[115][116][117].…”

Section: Photoinduced Electron Transfer Oxygenation Of Unsaturated Sumentioning

confidence: 99%

Photoinduced electron transfer oxygenations

Lopez

1990

Topics in Current Chemistry

View full text Add to dashboard Cite

Electron-transfer photooxygenation of tetraphenylallene formation of 1,3-dihydroperoxy-1, 1,3,3-tetraphenyl-2-propanone and its decomposition under chemiluminescence

Cited by 12 publications

References 19 publications

Some Typical Advances in the Synthetic Applications of Allenes

Some Typical Advances in the Synthetic Applications of Allenes

The Chemistry of Azetidin-3-ones, Oxetan-3-ones, and Thietan-3-ones

Photoinduced electron transfer oxygenations

Contact Info

Product

Resources

About