189

de Mayo reaction
[2 + 2] Photochemical cyclization of enones with olefins is followed by a retroaldol reaction to give 1,5-diketones.
O

CO2Me

CO2Me hQ
OH

OH

CO2Me

hQ, [2 + 2]
CO2Me
OH
head-to-tail alignment

OH

CO2Me

cycloaddition

O H

retro-aldol
cyclobutane cleavage
O

CO2Me

CO2Me

CO2Me

Minor regioisomer:
O

CO2Me

CO2Me

hQ, [2 + 2]
cycloaddition

OH

OH
head-to-head alignment

O H

O
CO2Me

retro-aldol

CO2Me

CO2Me

cyclobutane cleavage
O

190

Example 15
O

Ph

O
1. hQ, cyclohexane, 83%

2. H2 (3 atm), Pd/C (10%)

HOAc, rt, 18 h, 83%

O
Example 29
O

hQ, MeOH
> 90%
OH
O

HO H

H
O

References
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de Mayo, P.; Takeshita, H.; Sattar, A. B. M. A. Proc. Chem. Soc., London 1962, 119.
Paul de Mayo received his doctorate from Sir Derek Barton at Birkbeck College, University of London. He later became a professor at the University of Western Ontario
in London, Ontario, Canada, where he discovered the de Mayo reaction.
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