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• W1987116852 endingPage "1901" @default.
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• W1987116852 abstract "Durch direkte Anregung des polychromophoren anti-Pentaen-tetraesters 1 mit Licht der Wellenlänge λ>280 nm wird selektiv (75–80%) unter „diagonaler”︁ Beteiligung von vier Bindungen (formal [π2s + π2a + π2a + σ2s] der Nonacyclus 4 gebildet (neben 5–7% Octacyclus 5 und wenig 14). 4 entsteht über ein licht- (und wärme)-empfindliches Zwischenprodukt (12), welches sehr rasch unter Photo-[π2 + π2]-Addition weiterreagiert. Sensibilisierung durch Aceton bzw. Benzophenon manifestiert mit der Bildung von 14 und 18 eine effiziente Spinkorrelation. In 2 übt der Epoxidsauerstoff eine ungewöhnliche dirigierende Wirkung aus: Die intramolekulare [π2 + π2]-Cycloaddition zwischen extrem entfernten CC-Doppelbindungen (ca. 4.4 Å) zum thermisch labilen 24 konkurriert wirksam mit der zu 1→4 analogen Umwandlung zu 23 (direkte Anregung) bzw. ist ausschließlicher Reaktionsweg (sensibilisierte Anregung). Die Struktur des decacyclischen Photoproduktes 23 wird durch Röntgenstrukturanalyse bewiesen. On the Selectivity of Photochemical Processes in Polychromophoric Molecules A [π2s + π2a + π2a + σ2s]-Reaction? – An Unusual [π2+π2]-Cycloaddition Upon direct excitation of the „polychromophoric”︁ anti-pentaene-tetraester 1 with light of wavelength λ>280 nm with „diagonal”︁ participation of four bonds (formally [π2s + π2a + π2a + σ2s]) the nonacycle 4 is formed selectively (75–80% together with 5–7% of the octacycle 5 and a little 14). 4 arises via a light- (and heat)- sensitive intermediate (12), which is rapidly withdrawn in a photo-[π2 + π2]-addition. With the formation of 14 and 18 the acetone (benzophenone) sensitised reaction manifests an efficient spin correlation. The epoxide oxygen in 2 exerts an unusual directing effect: The intramolecular [π2 + π2]-cycloaddition between widely separated CC-double bonds (approx. 4.4 Å) effectively competes with conversion into 23 (analogous to 1→4) (direct excitation) or is the sole pathway (sensitised excitation). The structure of the decacyclic photoproduct 23 is established by x-ray analysis." @default.
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• W1987116852 date "1982-05-01" @default.
• W1987116852 modified "2023-10-01" @default.
• W1987116852 title "Zur Selektivität photochemischer Umwandlungen in polychromophoren Molekülen Eine [π2 _s + π2 _a + π2 _a + _σ 2 _s ]‐Reaktion? – Eine ungewöhnliche [π2 + π2]‐Cycloaddition" @default.
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• W1987116852 doi "https://doi.org/10.1002/cber.19821150519" @default.
• W1987116852 hasPublicationYear "1982" @default.
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