Mechanism and stereoselectivity of photosensitized oxygen transfer reactions

Gollnick, Klaus; Schenck, Günther O.

doi:10.1351/pac196409040507

Cited by 291 publications

(88 citation statements)

References 15 publications

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“…This transformation could introduce the hydroperoxy group and relocate the double bond of an olefin into the same positions as is observed in the photosensitized oxidation, eq. [2]. This paper reports some of the results obtained in the study of this approach.…”

Section: -Ohmentioning

confidence: 97%

“…[2] can, in fact, be used to transform 2,3-dimethyl-2-butene and 1 ,2-dimethylcyclohexene to the corresponding allylic hydroperoxides in good yield. The products are the same as those obtained from the photosensitized reaction, and in the case of 1,2-dimetl~ylcyclo-hexene even the selectivities of the two processes are similar.…”

Section: Reaction Of P-halol7ydroj1eroxides Wit12 Basementioning

confidence: 99%

“…[2] is thus seen to lead to the desired allylic hydroperoxide only with tetrasubstituted olefins where it works very well.…”

Section: Reaction Of P-halol7ydroj1eroxides Wit12 Basementioning

confidence: 99%

“…The dye-photosensitized oxidation of olefins affords a unique route to allylic hydroperoxides of definite structure (1,2). The hydroperoxy group is always introduced at one of the originally olefinic carbon atonls and a shift of the double bond always occurs, eq.…”

Section: Introductionmentioning

confidence: 99%

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Preparation and base-catalyzed reactions of some β-halohydroperoxides

Kopecky¹,

Sande²,

Mumford³

1968

Can. J. Chem.

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The reaction between olefins, N-chloroacetamide or 1,3-dibromo-5,5-dimethylhydantoin, and hydrogen peroxide affords p-halohydroperoxides in good yields. These conlpounds react extremely rapidly in basic solution to give products w~llich depend upon their structure. The 3-halo-2,3-dimethyl-2-butyl hydroperoxides form 2,3-dimethyl-3-llydroperoxy-1-butene and from the 2-halo-1,2-dimethylcyclohexyl hydroperoxides 1-methyl-2-methylene-cyclohexyl hydroperoxide is obtained. N o allylic hydroperoxide can be detected from the reaction between base and 3-bromo-2-methyl-2-butyl hydroperoxide. Mainly cleavage products, acetone and acetaldehyde, are formed together with some 2,3-epoxy-2-methylbutane. The reaction between base and 2-bromo-1-phenylethyl hydroperoxide gives styrene oxide, benzoic acid, and some benzaldehyde. From trorts-2-bromocyclol~exyl hydroperoxide, Iron.s-2-bron1ocyc1ohexano1, cyclohexene oxide, and some Irarls-l,2-cyclohexanediol are obtained upon reaction with base. N o evidence for the formation of the allylic hydroperoxide was obtained.

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Section: -Ohmentioning

confidence: 97%

Section: Reaction Of P-halol7ydroj1eroxides Wit12 Basementioning

confidence: 99%

“…[2] is thus seen to lead to the desired allylic hydroperoxide only with tetrasubstituted olefins where it works very well.…”

Section: Reaction Of P-halol7ydroj1eroxides Wit12 Basementioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Preparation and base-catalyzed reactions of some β-halohydroperoxides

Kopecky¹,

Sande²,

Mumford³

1968

Can. J. Chem.

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“…The quantum yields of triplet formation or the intersystem-crossing rates for eosin Y have been deduced from phosphorescence quantum yield and phosphorescence lifetime measurements in a spectrophosphorimeter [22], from sensitized photoreduction studies [24,25], and from absorption measurements using microsecond flash photolysis systems [26][27][28], a pulsed submicrosecond dye laser [29], and a repetitive subnanosecond dye laser [30].…”

Section: Introductionmentioning

confidence: 99%

Intersystem-crossing and excited-state absorption in eosin Y solutions determined by picosecond double pulse transient absorption measurements

Penzkofer

Beidoun

Daiber

1992

Journal of Luminescence

100

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Transformation of fenuron induced by photochemical excitation of humic acids

Aguer

Richard

1996

Pestic. Sci.

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When neutral solutions containing the herbicide 3-phenyl-1,ldimethylurea (fenuron) and a humic acid are irradiated at 365 nm, 3-(4-hydroxypheny1)-1,l-dimethylurea and three biphenyl products are formed as main products. The apparent quantum yield of fenuron disappearance is evaluated as 6.2 x 10-5mole E-'.Upon irradiation of the same mixture at 253.7 nm, both direct and induced phototransformations of fenuron occur. Direct photooxidation yields 2-and 4-amino-N,N-dimethylbenzamide. The induced phototransformation leads to 2-and 4-hydroxylation of the aromatic ring in accordance with the fact that hydroxyl radicals are involved in the oxidation.

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Mechanism and stereoselectivity of photosensitized oxygen transfer reactions

Abstract: Abstract

Cited by 291 publications

References 15 publications

Preparation and base-catalyzed reactions of some β-halohydroperoxides

Preparation and base-catalyzed reactions of some β-halohydroperoxides

Intersystem-crossing and excited-state absorption in eosin Y solutions determined by picosecond double pulse transient absorption measurements

Transformation of fenuron induced by photochemical excitation of humic acids

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