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H
O
O
H
P
P
R 2
R 2
O
O
O 2
O
O
O
R 1
R 2
R 1
R 1
R 2
R 1
P
P
BF 3 . EtO 2
UV
Scheme 4.32 Use of phospha-Michael addition to make bio-based polymers with improved flame-retardant properties. 72
OH
O TBDMS
OH
O H
O
O TBDMS
(RO) 2 HPO
1% HCl in
Castor oil
(Lesquerella oil)
H
(RO) 2 P
(RO) 2 P
n
5
95% EtOH
n
5
NaOMe,
-40 °C, THF
n
5
O
O
Scheme 4.33 Use of the Abramov reaction to form castor- (n ¼ 7) and lesquerella- (n ¼ 9) based a-hydroxy phosphonates. 73,74 The reaction
was also carried out with FAs, where the C ¼ C bond had been saturated. TBDMS: tert-butyldimethylsilyl.
 
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