Table 1.

Effect of electron relays as an additive in the [2 + 2] dimerization of anethole^a

Entry	Electron relayb	Equivalents	Yield
1	None	None	0%
2	Anthracene (+1.21 V)	0.25	13%
3	Naphthalene (+1.61 V)	0.25	16%
4	Naphthalene	0.5	18%
5 c	Naphthalene	0.5	54%
6	NPh3 (+0.91 V)	0.25	0%
7d	Naphthalene	0.5	0%
8e	Naphthalene	0.5	0%

^aReactions were carried out for 24 h, unless otherwise noted. ¹H NMR yields are reported.

^bPeak potentials of electron relay in parenthesis.

^cReaction time was 5 days.

^dReaction in the dark.

^eReaction in the absence of p-OMeTPT.