Table 1 GTP of cinnamates and their derivatives with MTS in the presence of various organic acid catalysts^a

Entry	Monomer	Initiator (mmol)	Catalyst (mmol)		CH₂Cl₂ (mL)	Temp (°C)	Time (day)	Polymer yield (%)	M_n^b (g mol⁻¹)	Đ^b (M_w/M_n)
1	Methyl cinnamate	0.26	Tf₂NTMS	0.26	7.5	rt	7	23	7,300	1.60
2	Methyl cinnamate	0.26	Tf₂NTMS	0.26	7.5	0	7	34	12,000	1.81
3	Methyl cinnamate	0.26	Tf₂NTMS	0.26	7.5	−20	7	46	12,200	1.84
4	Methyl cinnamate	0.26	Tf₂NTMS	0.26	7.5	−35	7	43	13,000	1.47
5	Methyl cinnamate	0.26	Tf₂NTMS	0.26	7.5	−35	14	69	15,000	1.69
6	Methyl cinnamate	0.33	Tf₂NTMS	0.26	7.5	−35	14	84	14,400	1.37
7	Methyl cinnamate	0.37	Tf₂NTMS	0.26	7.5	−35	14	89	12,200	1.41
8	Methyl cinnamate	0.43	Tf₂NTMS	0.26	7.5	−35	14	88	9,500	1.48
9	Methyl cinnamate	0.52	Tf₂NTMS	0.26	7.5	−35	14	85	7,500	1.49
10	Methyl cinnamate	0.26	Tf₂NTMS	0.26	7.5	−35	28	81	18,100	1.90
11	Methyl cinnamate	0.26	Tf₂NTMS	1.30	7.5	−35	7	75	17,800	1.73
12	Methyl cinnamate	0.26	Tf₂NTMS	0.05	12.5	−35	7	22	4,200	1.27
13	Methyl cinnamate	0.26	C₆F₅CHTf₂	0.05	12.5	−35	7	9	4,600	1.30
14	Methyl cinnamate	0.26	Tf₂NH	0.05	12.5	−35	7	14	4,500	1.27
15	Methyl cinnamate	0.26	Ph₃C[B(C₆F₅)₄]	0.05	12.5	−35	7	8	4,200	1.28
16	Methyl cinnamate	0.26	Tf₂NTMS	0.26	12.5	−35	7	35	7,300	1.27
17	Ethyl cinnamate	0.26	Tf₂NTMS	0.26	12.5	−35	7	6	3,800	1.10
18	Isopropyl cinnamate	0.26	Tf₂NTMS	0.26	12.5	−35	7	trace	800	1.06
19	Methyl 4-methyl cinnamate	0.26	Tf₂NTMS	0.26	12.5	−35	7	35	8,300	1.16
20	Methyl 4-methoxy cinnamate	0.26	Tf₂NTMS	0.26	12.5	−35	7	66	3,000	1.48
21	Methyl 3,4-dimethoxy cinnamate	0.26	Tf₂NTMS	0.26	12.5	−35	7	none^c	−	−
22	Methyl 3,4,5-trimethoxy cinnamate	0.26	Tf₂NTMS	0.26	12.5	−35	7	none^c	−	−

^aMonomer, 13 mmol. All experiments were performed in a dry argon atmosphere
^bNumber-average molecular weight (M_n) and dispersity (Đ) were determined using conventional GPC against PSt standards in CHCl₃
^cPolymer was not obtained

Quick links

Search