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The order of first bond formation in the intramolecular photocycloaddition of 2-(4′-pentenyl)-cyclohex-2-enones

✍ Scribed by Nizar Haddad; Nitsa Galili

Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
227 KB
Volume
38
Category
Article
ISSN
0040-4039

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✦ Synopsis

Complete trapping of 1,4-diradical intermediates, formed in the photocycloaddition of 9, provide direct evidence that first bond formation takes place at either C(ct) or C(13) positions of the cyclic enone. No cleavage of the 1,4-diradical 10 or endo-diradical intermediates 11 and 12 could be detected. However, partial cleavage of the exo-dirac~eal inmates 13 and 14 was measured. Unusual long-range aromatic radical substitution was obtained m a competing rate with the eyeloprepyl earbinyl radical rearrangement.

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Highly efficient trapping of short-lived
Highly efficient trapping of short-lived 1,4-diradicals, the order of first bond formation in the intramolecular photocycloaddition of 3-(4′-pentenyl)-cyclohex-2-enones
✍ Dan Becker; Nitsa Galili; Nizar Haddad 📂 Article 📅 1996 🏛 Elsevier Science 🌐 French ⚖ 264 KB

Complete trapping of 1.4~diradical intermediates, formed in the intramolecular [2+2] photocycloaddition of 13. provide direct evidence for the exclusive formation of the first bond at the C(8) of the cyclic enone. This result is found in full agreement with the previously studied compounds 1. Copyr

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## Abstract n‐π^\*^ Excitation of 6‐fluoro‐4,4‐dimethyl‐2‐cyclohexenone in the presence of 2,3‐dimethyl‐2‐butene leads selectively to the formation of the corresponding oxetane. The factors which influence the oxetane __vs.__ cyclobutane formation ratio in photoadditions of cyclic enones to olefins