Table 1.

Reaction optimization of one-pot synthesis for aliphatic diazirine 2a ^a.

Entry	Solvent	Base	Temp	Yield (%) b
1	NH3	LiNH2	RT	36
2	NH3	NaNH2	RT	44
3	NH3	NaH	RT	47
4	NH3	MgH2	RT	20
5	NH3	CaH2	RT	17
6	NH3	EtONa	RT	45
7	NH3	MeONa	RT	45
8	NH3	MeOK	RT	63
9	NH3	NaOH	RT	28
10	NH3	KOH	RT	67
11	NH3	KOH	0 °C	11
12	NH3/MeOH c	KOH	RT	5

^a Unless otherwise mentioned, 1a (2 mmol) and NH₂OSO₃H (1.1 equiv.) was added to liquid ammonia (8 mL) at −78 °C and the reaction mixture was stirred at room temperature for 12 h until base (3.3 equiv.) was added. After the addition of base, the reaction was further stirred at room temperature under air for 2 h. ^b Isolated yields were presented. ^c Ammonia gas was bubbled into MeOH (8 mL) at 0 °C for 30 min.