Table 2.

Photoinduced 1,3-Dipolar Cycloaddition Reactions of Macrocyclic and Acylic Tetrazoles with Alkenes^[a].

entry	alkene	tetrazole	pyrazoline	time[b] (min)	yield[c] (%)
1		2	2a	120	59
2		3	3a	75	71
3		4	4a	84	60
4		5	5a	180	70
5		6	6a	120	46[d]
6		9	9a	300	43
7		10	10a	120	58
8		2	2b	108	95
9		3	3b	54	91
10		4	4b	120	81
11		5	5b	240	60
12		6	6b	90	84
13		9	9b	120	84
14		10	10b	60	76

^[a]Reactions were conducted by irradiating 0.1 mmol of tetrazole and 10 mmol of alkene dipolarophile in 250 mL EtOAc with a 302-nm UV lamp in quartz flask.

^[b]Time was determined by tracing the disappearance of the starting materials on TLC.

^[c]Isolated yields.

^[d]The pyrazoline adduct was unstable upon standing.