. Author manuscript; available in PMC: 2008 Aug 15.

Published in final edited form as: J Org Chem. 2006 Oct 13;71(21):8183–8189. doi: 10.1021/jo0614902

Table 4.

Selectivity in Diazo Decomposition of 8 with a Na⁺ Template^a

Catalyst	NaBPh₄ (mol %)	11:12^b	E:Z (11)^b	Yield (11 + 12), %^c
Rh₂(OAc)₄	110	100:0	35:65	45
(1.0 mol %)	80	100:0	38:62	47
	10	100:0	35:65	61
	0	100:0	36:64	71
Cu(CH₃CN)₄PF₆	110	100:0	^d	49
(10 mol %)	80	100:0	80:20	55
	10	63:37	72:38	73
	0	51:49	57:43	82

Decomposition carried out as 2 h addition of catalyst in dichloromethane to a refluxing dichloromethane solution of 8 and sodium tetraphenylborate.

Ratios of products obtained by ¹H NMR. Variability ± 3%.

Yields obtained are based on proton NMR data and assume complete mass recovery after filtration.

Not determined.