Chemistry Reference
In-Depth Information
The reaction of 2-bromomestylene (BrC
6
H
2
Me
3
) with N-bromosuccinimide and
dibenzoyl peroxide in HCO
2
Me gave (26%) 2,4,6-tris(bromomethyl)bromobenzene,
which when treated with thiourea generated 2,4,6-tris(isothiouroniummethyl)bro-
mobenzene tribromide [122].
2,4,6-Tris(hydroxymethyl)aniline has been shown to possesses a drug [123] or
reporter [124,125] properties at the dendron's surface by the incorporation of an
enzyme substrate or H
2
O
2
trigger at the focal position, respectively. The treatment of
1,3,5-tris(hydroxymethyl)benzene with tert-butyldimethylsilyl chloride gave
C
6
H
3
(CH
2
OTBS)
3
, which was nitrated and reduced to the tris-O-protected aniline,
which was transformed to the corresponding isocyanate, OCNC
6
H
2
(CH
2
OTBS)
3
[124,126]. This isocyanate was reacted with a substituted phenol and the resultant
carbamate was O-deprotected free-up the hydroxymethyl moieties for further
elaboration.
2,4,6-Tris(formyl)phenol [127] was prepared (48-54%) or by the reaction of either
4-hydroxybenzaldehyde or phenol with HMTA in trifluoroacetic acid. Treatment of
2,4,6-tris(formyl)phenol with the chlorocarbamoyl of N,N
0
-dimethylethylenediamine
