Addition of singlet oxygen to arene oxides

Foster, Charles H.; Berchtold, Glenn A.

doi:10.1021/jo00913a027

Cited by 50 publications

(12 citation statements)

References 13 publications

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“…25 The endoperoxide 50 could not be isolated. The intervention of 50 has been postulated by isolation of the bisepoxide 51 and keto epoxide 52 which are derivatives of 50 (eq. 10).…”

Section: Reduction Of Bicyclic Endoperoxidesmentioning

confidence: 99%

“…They found that bases such as potassium hydroxide, sodium ethoxide, or piperidine catalyze the decomposition of 1-phenylethyl fert-butyl peroxide (169) (eq 52). C(CH3)3OH (52) In view of this mechanism, only those dialkyl peroxides and alkyl hydroperoxides having a hydrogen on the carbon attached to the peroxide linkage should undergo base-catalyzed rearrangement.…”

Section: Rearrangement Of Endoperoxidesmentioning

confidence: 99%

See 1 more Smart Citation

Bicyclic endoperoxides and synthetic applications

Balcı¹

1981

Chem. Rev.

246

108

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“…25 The endoperoxide 50 could not be isolated. The intervention of 50 has been postulated by isolation of the bisepoxide 51 and keto epoxide 52 which are derivatives of 50 (eq. 10).…”

Section: Reduction Of Bicyclic Endoperoxidesmentioning

confidence: 99%

Section: Rearrangement Of Endoperoxidesmentioning

confidence: 99%

Bicyclic endoperoxides and synthetic applications

Balcı¹

1981

Chem. Rev.

246

108

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“…For 10s: mp 162-163.5 °C; IR (Nujol) 3450 (s), 3400 (s), 3320 (s), 1100 (s), 1090 (s) cm"1; NMR (CDC13) 1.37 (s, 6 ), 1.57 (s, 6 H), 2.27 (br s, 2 ), 7.0-7.3 (m, 2 H), 7.3-7.6 (m, 2 H); mass spectrum, m/e (rel. intensity) 234 (4), 200 (8), 173 (100).…”

Section: Experimental Section35mentioning

confidence: 99%

Endoperoxides of naphthalenes. Synthesis and reactions of substituted 2,3-epoxynaphthalene 1,4-endoperoxides

Sasaoka¹,

Hart²

1979

J. Org. Chem.

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“…20 Mechanistically this reaction can be viewed as a double halogenation of a 1,1-diol. 1b, 11 This offers an alternative protocol to generate singlet oxygen for more sensitive substrates that are not suitable to subject to more traditional singlet oxygen conditions. 22 Deacylation of N-monosubstituted amides was reported employing an in situ generated triphenyl phosphite chlorine complex (eq 11).…”

Section: Conversion Of Alcohols To Halidesmentioning

confidence: 99%

Triphenyl Phosphite

Gallagher¹,

Crawley²

2007

Encyclopedia of Reagents for Organic Synthesis

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PhO) 3 P [101-02-0] C 18 H 15 O 3 P (MW 310.30) InChI = 1/C18H15O3P/c1--15H InChIKey = HVLLSGMXQDNUAL-UHFFFAOYAF (mildly nucleophilic phosphite for converting alcohols to alkyl halides; 3 coupling agent in peptide and related syntheses, 1b,12 as its ozone adduct, a low-temperature source of singlet oxygen 1b ) Physical Data: mp 22-25 • C; bp 360 • C, 180-189 • C/1 mmHg; n 25 D 1.5890; δ 31 P 125-129. Solubility: insol H 2 O (hydrolyzes to (PhO) 2 P(O)H); miscible most organic solvents; alcoholic solvents may transesterify. Form Supplied in: colorless liquid, 97% pure, widely available, showing only one peak in 31 P NMR. The balance is largely phenol. Purification: an ethereal solution is washed with aqueous alkali, dried, and distilled. Handling, Storage, and Precautions: fairly safe to handle, but itis a skin sensitizer and will usually contain phenol.General Discussion. The ester converts alcohols to alkyl halides in the presence of a hydrogen halide, a halogen, or another alkyl halide (eqs 1 and 2), the two last being mild and convenient procedures. 2,3 Good yields are obtained, even with neopentyl halides, and the reaction proceeds with inversion at carbon. 4 The intermediate phosphonium salts may be prepared independently but are very susceptible to hydrolysis and are conveniently generated and used as required. Methyltriphenoxyphosphonium iodide has also found use in the deoxygenation of epoxides 5 (with retention of stereochemistry) and the dehydration of secondary alcohols. 6 Phenyl esters of carboxylic acids can be made from the salts and a carboxylate ion 7 or from the free acid and the neutral ester 8 (eqs 3 and 4). Phosphorus 9 and sulfur 10 acids may be esterified similarly.

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Addition of singlet oxygen to arene oxides

Cited by 50 publications

References 13 publications

Bicyclic endoperoxides and synthetic applications

Bicyclic endoperoxides and synthetic applications

Endoperoxides of naphthalenes. Synthesis and reactions of substituted 2,3-epoxynaphthalene 1,4-endoperoxides

Triphenyl Phosphite

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