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N
N
B
O
O
B
O
O
OO
O
O
CHO
O
O
B
B
O
O
B
(HO)
2
B
47
N
N
N
NH
2
OH OH
50
NH
2
3
+
2
OH OH
H
2
N
49
48
OHC
N
N
N
51
B(OH)
2
B
O
B
O
O
O
OO
O
O
O
O
B
B
O
O
B
N
N
N
52
Scheme 1.55 One-pot multicomponent reaction for the synthesis of the cages 50
and 52 under ball milling.
developed several methods where rotaxanes can be synthesized by ball-
milling in solid state with high yields. The solid state condensation of 1,8-
diaminonaphthalene and benzaldehyde under ball milling provides an
ecient, waste-free procedure for synthesizing interlocked molecules such
as [2]- and [4]-rotaxanes due to the steric bulk and stability of the resulting
dihydropyrimidine stopper units (Scheme 1.57).
54
Furthermore, with rotaxane preparation, the smallest rotaxane was
achieved in a ball mill by utilizing the Diels-Alder reaction of 1,2,4,5-tetra-
zine with the terminal alkyne units of a 21-crown-7 (21C7)-based
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