Application of electron spin resonance spectroscopy to problems of structure and conformation. XXX. Aliphatic semidiones. XXXI. Conjugated singly unsaturated 1,2-semidiones in carbocyclic systems

Russell, Glen A.; Blankespoor, Ronald L.; Trahanovsky, Kathleen D.; Chung, C.‐S.; Whittle, Philip R.; Mattox, John; Myers, Charles L.; Penny, Robert; Ku, Thomas W.

doi:10.1021/ja00840a050

Cited by 25 publications

(2 citation statements)

References 6 publications

(6 reference statements)

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“…cis,trans -10b : Yield: 4.9%; colorless crytals; mp 126−148 °C (lit 17a. mp 152 °C for trans - 10b diastereomer, but stereochemistry based only on chemical properties); R f = 0.24.…”

Section: Methodsmentioning

confidence: 99%

“…Although the 3-hydroxychromanone skeleton is also a frequent structural unit of various natural products, only a few synthetic methods have hitherto been developed. Lead tetraacetate-mediated acetoxylation of chromanones offers a useful approach but occasional difficulties in the hydrolysis of the resulting 3-acetoxychromanones have been reported 17a. A more elegant and enantioselective hydroxylation of 3-substituted chromanone enolates by sulfonyloxaziridines was published recently by Davis and co-workers .…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and Cyclization of 1-(2-Hydroxyphenyl)-2-propen-1-one Epoxides: 3-Hydroxychromanones and -flavanones versus 2-(1-Hydroxyalkyl)-3-coumaranones

et al. 1996

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Competitive α and β cyclization of 2‘-hydroxychalcone epoxides affords 2-(α-hydroxybenzyl)-3-coumaranone and/or 3-hydroxyflavanones, which depends on the conditions employed. Epoxidation of 2‘-hydroxychalcones by dimethyldioxirane followed by either base- or acid-catalyzed ring closure provides a novel, general, and efficient method for the synthesis of trans-3-hydroxyflavanones, which includes also the naturally occurring derivatives. Extension of this two-step procedure to 1-(2-hydroxyphenyl)-2-alken-1-ones was also accomplished. A strong preference for α cyclization was observed in the case of β-unsubstituted or -monoalkylated α,β-enones, while both 2,2-dimethyl-3-hydroxychromanones and 2-(1-hydroxy-1-methylethyl)-3-coumaranones were obtained from the β,β-dimethylated substrates.

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“…cis,trans -10b : Yield: 4.9%; colorless crytals; mp 126−148 °C (lit 17a. mp 152 °C for trans - 10b diastereomer, but stereochemistry based only on chemical properties); R f = 0.24.…”

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis and Cyclization of 1-(2-Hydroxyphenyl)-2-propen-1-one Epoxides: 3-Hydroxychromanones and -flavanones versus 2-(1-Hydroxyalkyl)-3-coumaranones

et al. 1996

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Mehrstufige organische Redoxysteme — ein allgemeines Strukturprinzip

Deuchert¹,

Hünig²

1978

Angew. Chem.

159

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Multistage Organic Redox Systems—A General Structural Principle

Deuchert

Hünig

1978

Angew. Chem. Int. Ed. Engl.

280

149

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A general structural principle for organic compounds that have the capacity for two-stage electron transfer is based on the following reaction sequence:X+CH=CHj,X 5 In this scheme one or both of the entities X may be replaced by Y'. The radical partners in these systems often have very high thermodynamic stability. The choice of the end groups X and Y, (partial) inclusion of n-systems in rings, alteration of the number of vinylene groups,

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Application of electron spin resonance spectroscopy to problems of structure and conformation. XXX. Aliphatic semidiones. XXXI. Conjugated singly unsaturated 1,2-semidiones in carbocyclic systems

Cited by 25 publications

References 6 publications

Synthesis and Cyclization of 1-(2-Hydroxyphenyl)-2-propen-1-one Epoxides: 3-Hydroxychromanones and -flavanones versus 2-(1-Hydroxyalkyl)-3-coumaranones

Synthesis and Cyclization of 1-(2-Hydroxyphenyl)-2-propen-1-one Epoxides: 3-Hydroxychromanones and -flavanones versus 2-(1-Hydroxyalkyl)-3-coumaranones

Mehrstufige organische Redoxysteme — ein allgemeines Strukturprinzip

Multistage Organic Redox Systems—A General Structural Principle

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