Table 1 Aminolysis reaction of (R)-(+)-limonene oxide with different aminesa.

From: Cyclic carbamates based on (R)-(+)-limonene oxide for ring-opening polymerization

figure a

Entry

Amine

2 (%)b

2’ (%)b

Yield %

1

Methylamine

53

47

97

2

Hexylamine

100

n.d.c

50

3

Benzylamine

100

n.d.

50

4

Aniline

73

27

59

  1. aReaction conditions: (R)-(+)-limonene oxide (1 eq.), amine (2 eq. for entries 1 and 4, 1.2 eq. for entries 2,3), water, 100 °C, 24 h.
  2. bCalculated by integrating the signals in the 1H NMR spectrum of the crude reaction mixture and by considering their relative abundance. Not detected.
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