Chlorinating agent and FAC effects on the selective catalytic chlorination of carvone a^a,c.

Chlorinating agent	Catalyst amount (eq.)	Time (h)	Conversion a (%)	Monochloride b (%)	Dichloride c (%)	Vinyl allyl dichloride d (%)	Trichloride e (%)
NCS	Catalyst-free	0.5	NR	NR	NR	NR	NR
		24	34	74	26	—	—
	0.5	0.5	NR	NR	NR	NR	NR
		24	52	46	54	—	—
	2.5	0.5	Trace	Trace	—	—	—
		24	58	30	61	9	—
NaDCC	Catalyst-free	0.5	Trace	Trace	—	—	—
	0.5	0.5	100	97	2	—	—
	2.5	0.5	100	Trace	8	78	9
NaClOb	Catalyst-free	0.5	NR	NR	NR	NR	NR
	0.5	0.5	7	100	—	—	—
	2.5	0.5	100	56	12	32	6

^aReaction conditions: FeCl₂ (in 5 mL H₂O), chlorinating agent (4 eq. in 5 mL H₂O), CH₂Cl₂/H₂O (10 mL (5 : 5)), RT. Conversion was determined by GC using an internal standard.

^b5–10% FAC.

^cNR: no reaction.