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. Author manuscript; available in PMC: 2008 Sep 7.
Published in final edited form as: J Am Chem Soc. 2006 Jun 7;128(22):7315–7319. doi: 10.1021/ja060968g

Table 2.

Solvent dependant intramolecular [2+2] photocycloadditions

entry enone products solvent/yield/ratio
(1) graphic file with name nihms-61089-t0011.jpg graphic file with name nihms-61089-t0012.jpg graphic file with name nihms-61089-t0013.jpg CH2Cl2 80% 14a/14b (1:6)
acetone/H2O 60% 14a/14b (>20:1)
(2) graphic file with name nihms-61089-t0014.jpg graphic file with name nihms-61089-t0015.jpg CH2Cl2 89% (81% conv.)
MeOH 60% (87% conv.)
(3) graphic file with name nihms-61089-t0016.jpg graphic file with name nihms-61089-t0017.jpg graphic file with name nihms-61089-t0018.jpg CH2Cl2 72% 18a/18b (1:4)
acetone/H2O 74% 18a/18b (6:1)
(4) graphic file with name nihms-61089-t0019.jpg graphic file with name nihms-61089-t0020.jpg graphic file with name nihms-61089-t0021.jpg CH2Cl2 47% 19a/19b (>1:20)
acetone/H2O 38% 19a/19b (>20:1)
(5) graphic file with name nihms-61089-t0022.jpg graphic file with name nihms-61089-t0023.jpg graphic file with name nihms-61089-t0024.jpg CH2Cl2 21% 20a/20b(1:10)
acetone/H2O 40% 20a/20b (16:1)

All reactions: hv, Pyrex filter, 3mM in solvent.