Preparative Organic Photochemistry by J. -M. Lehn (eds.)

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By J. -M. Lehn (eds.)

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E. addition of the carbonyl group of the enone to an olefin is also observed 452~. b). 44). 46)458~. 47). 48). 3 Photocycloadditions to the C - - C Double Bond O O ~cH3o. 52) 464). 53)465), are valuable synthons in organic chemistry 4544). 55) have been obtained via addition of 6-isopropyl-3-methyl-2-cyclohexenone to cyclobutene derivatives. 56)468). 0 0 + _ b y ...... 01'4]octane 469,). 58) 469b). 59) 470). 61) have also been synthesized via intermolecular cycloaddition reactions. 61) \ 54 4 Photoaddition Reactions in Synthetic Organic Chemistry 3(2H)-furanones undergo efficient cycloadditions as "oxa-enones" 450).

3) H Another important feature of this reaction is the synthesis of highly strained E-cycloalkenes. 5) 31o). 6) 311). 1 Photorearrangements hexene. 8)313). 7) ~C6H5 hv ~C6H5 Sens, --- • -I- Sens. 2 Electrocyclic Reactions of Conjugated Dienes and Trienes Electrocyclic reactions were first described by Woodward and Hoffmann in their classic series of articles. 13) 321). 3 Di-pi-methane Rearrangement of 1,4-Dienes 1,4-Dienes can be converted photochemically to vinyl cyclopropanes. This reaction, also named the Zimmerman rearrangement 322), is common to molecules in which two n moieties are substituents on a "methane" carbon 323).

7)407). 02"5]hexane skeleton is formed. 8) 4 Photoaddition Reactions in Synthetic Organic Chemistry If no ~,-H atom is available, or if for steric reasons abstraction of a 8-H atom is facilitated, this latter reaction occurs with formation of a cyclopentanol. A series of such sequences has been used in the synthesis of dodecahedrane 409a,b) at,13-Unsaturated ketones afford cyclohexanones instead of cyclobutanols as one of the radical centres in the originally formed 1,4-diradical is an allylic moiety.

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