Skip to main content
. Author manuscript; available in PMC: 2009 Dec 5.
Published in final edited form as: J Org Chem. 2008 Dec 5;73(23):9479–9481. doi: 10.1021/jo8017704

Table 1.

Bicyclic and Tricylic Diazenes

Entry Ketone Diazene Yield (%)a
1 graphic file with name nihms91168t1.jpg
1a
graphic file with name nihms91168t2.jpg
2ab
84
2 graphic file with name nihms91168t3.jpg
1bc
graphic file with name nihms91168t4.jpg
2b
76
3 graphic file with name nihms91168t5.jpg
1cd
graphic file with name nihms91168t6.jpg
2ce
70
4 graphic file with name nihms91168t7.jpg
1d
graphic file with name nihms91168t8.jpg
2d
68
5 graphic file with name nihms91168t9.jpg
1e
graphic file with name nihms91168t10.jpg
2ef
91
6 graphic file with name nihms91168t11.jpg
1f
graphic file with name nihms91168t12.jpg
1fg
72
7 graphic file with name nihms91168t13.jpg
1g
graphic file with name nihms91168t14.jpg
2g
68
a

Yields are for pure isolated products.

b

The product was a ~ 5:1 mixture of diastereomers.

c

Ar = 4-methoxyphenyl.

d

The alkene was a ~ 5: 1 Z/E mixture.

e

The product was a ~ 5:1 mixture of diastereomers.

f

The product was a ~ 6:1 mixture of diastereomers. The major product had a 13C NMR methine at δ = 100.2. The minor diastereomer 13C NMR methine was at δ = 95.1

g

The product was a ~ 1:1 mixture of diastereomers.