Table 2 Tandem synthesis of aliphatic polyesters.

From: Tandem synthesis of alternating polyesters from renewable resources

Entry

Complex

Anhydride

Epoxide

[PPNCl]/[M]

[A]/[E]

Temperature (°C)

Time (h)

Yield (%)*

M n (g mol −1 )†

PDI†

1

1

CA

PO

—

15

30

24

<5

ND‡

ND‡

2

1

CA

PO

1

15

30

24

100

16,900

1.2

3

1

SA

PO

1

13.5

30

7.5

82

5,100

1.1

4

1

GA

PO

1

13.5

30

6

70

3,700

1.1

5

1

PA

PO

1.5

13.5

30

7.5

76

5,200

1.3

6

2

CA

PO

1

15

30

20

68

9,500

1.2

7

3

CA

PO

1

15

30

6.5

33

5,700

1.1

8

4

CA

PO

1

15

30

20

17

4,300

1.1

9§

1

CA

CHO

2

1

70

36

26

8,500

1.2

10§

3

CA

CHO

2

1

70

36

48

6,300

1.6

11§

2

CA

CHO

2

1

70

36

59

8,900

1.3

12§

3

CA

LO

2

1

100

28

29

8,500

1.2

13§

2

CA

LO

2

1

100

28

85

9,700

1.2

14§

2

CA

LO

1

1

100

120

12

5,900

1.1

15§

2

CA

LO

5

1

100

24

74

10,300

1.3

16

2

CA

LO

5

10

100

9

100

8,100

1.3

17║

2

GA

PiO

5

5

100

2

29

8,400

1.2

18¶

2

CA

LO

2

4

100

45

47

27,000

1.2

  1. Abbreviations: CA, camphoric anhydride; GA, glutaric anhydride; PA, pimelic anhydride; SA, succinic anhydride; .
  2. All reactions were performed after the cyclization step with [anhydride]/[M]=100 (except for entries 17 and 18).
  3. *As determined by the integration of 1H NMR.
  4. †Mn and PDI (Mw/Mn) of the polymer determined by SEC-RI in tetrahydrofuran at room temperature using polystyrene standards.
  5. ‡Not determined.
  6. §Reaction performed in toluene.
  7. ║Reaction performed with [anhydride]/[M]=200.
  8. ¶Reaction performed with [anhydride]/[M]=300.
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