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. Author manuscript; available in PMC: 2010 Jun 4.
Published in final edited form as: Org Lett. 2009 Jun 4;11(11):2285–2288. doi: 10.1021/ol900590t

Table 1.

Conditions for oxidative cycloaddition of 12.

graphic file with name nihms121381t1.jpg
entry oxidant (equiv)a solvent time (h) % yield
1 Mn(OAc)3 (2.1) AcOH 4 66b
Cu(OAc)2 (1.0)
2 Mn(OAc)3 (1.0) AcOH 6 31d
Cu(OAc)2 (1.0)
3 Mn(OAc)3 (2.1) AcOH 16 tracec
4 Cu(OAc)2 (1.0) AcOH 16 --d
5 Mn(OAc)3 (0.1) AcOH 16 traced
6 Mn(OAc)3 (2.1) THF 16 --c
Cu(OAc)2 (1.0)
7 Mn(OAc)3 (2.1) MeCN 16 --c
Cu(OAc)2 (1.0)
8 Ce(NH4)2(NO3)6 (2.0) MeCN 3 --e
9 PhI(OAc)2 (1.2) MeCN 16 NRd
a

All reactions were carried out at ambient temperature except when noted; Mn(OAc)3·2H2O, and Cu(OAc)2·H2O were used;

b

Isolated as a 5:1 mixture of olefin isomers (1H NMR);

c

Slow decomposition of the starting material occurred.

d

Starting material was recovered unreacted.

e

Reaction performed at −20 °C and resulted in a complex mixture of products.