Über die Konstitution der Photodimerisate der Cumarine und Furocumarine

Wessely, F.; Plaichinger, Ilse

doi:10.1002/cber.19420750807

Cited by 8 publications

(5 citation statements)

References 7 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…[19][20][21][22] However, much less is known about furocoumarins. For both pimpinellin (5,6-dimethoxyangelicin) 17 and 8-methoxypsoralen (8-MOP), 18 two isomeric compounds are obtained, which the authors assign as syn (structures 4 and 6) and anti (structures 5 and 7), without establishing the cis or trans configurations.…”

Section: Photoaddition Reactionsmentioning

confidence: 99%

“…By irradiating 4,5Ј,8-trimethylpsoralen (TMP), the authors isolated a pyrone-pyrone dimer (16) which, in agreement with Krauch's work on 8-MOP, 23 was assigned the trans-anti configuration by means of NMR experiments carried out in the presence of shift reagents. A pyrone-furan dimer of cis-syn structure was also isolated (17) which, on further UVA illumination, was converted into a bicyclomer (18). This is a cage compound in which two cyclobutane rings are present, each involving the pyrone ring of one monomer and the furan ring of the other, both in the cis-syn configuration.…”

Section: Photoaddition Reactionsmentioning

confidence: 99%

See 1 more Smart Citation

Furocoumarin photolysis: chemical and biological aspects

Caffieri

2002

Photochem Photobiol Sci

View full text Add to dashboard Cite

Furocoumarins (psoralens) undergo photolysis when subjected to UVA radiation in solution. Several products are formed, depending on the molecular structure and experimental conditions. Some products are the result of anoxic mechanisms (cyclodimerisation, addition of solvent), others of oxic pathways, leading to oxidised products. The mechanisms thought to underlie photolysis are described and the possible biological relevance of the photoproducts and intermediates is discussed.

show abstract

Section: Photoaddition Reactionsmentioning

confidence: 99%

Section: Photoaddition Reactionsmentioning

confidence: 99%

Furocoumarin photolysis: chemical and biological aspects

Caffieri

2002

Photochem Photobiol Sci

View full text Add to dashboard Cite

show abstract

“…The photochemical [2+2] dimerization of 2-oxo-2 H -1-benzopyrans (coumarins) is well known [ 1 , 2 , 3 , 4 , 5 , 6 , 7 ]. Over the last few years there has been a growing interest in some coumarin photodimers due to their applications in organic synthesis [ 8 , 9 , 10 ], in medicine [ 11 , 12 , 13 ] and in other modern technologies [ 14 , 15 , 16 ].…”

Section: Introductionmentioning

confidence: 99%

Regio- and Stereoselective [2+2] Photodimerization of 3-Substituted 2-Alkoxy-2-oxo-2H-1,2-benzoxaphosphorines

et al. 2002

View full text Add to dashboard Cite

Diethyl 1,2-benzoxaphosphorine-3-carboxylates 5 undergo a regio- and stereoselective [2+2] photodimerization reaction in methanol solution under the action of sunlight, giving in all cases the corresponding anti head-to-tail dimers 6 and 7. Concerning the stereogenic P atom, the photodimerization is also stereoselective, and the centrosymmetric stereoisomer 6 predominates over the non symmetric P-epimer 7.

show abstract

“…These are of interest, as the photodimer of o-hpdroxy-trans-cinnamic acid has been reported t o cyclize t o a dilactone, 11, n1.p. 320" (19,20), which is isomeric with the photodimer of coumarin.…”

mentioning

confidence: 99%

“…The photodilners of the substituted cinnamic acids were prepared by irradiation of the crystalline acids with sunlight (19,21), or with ultraviolet light (20). The photodimer of the o-hydroxy acid I X was reported t o inelt a t 320°, which is undoubtedly not its true inelting poifit, hut the melting point of the cyclized dilactone 11.…”

mentioning

confidence: 99%