Synthesis and reactions of p-vinylbenzyltris(trimethylsilyl)methane

Article abstract of DOI:10.1016/j.jorganchem.2004.08.032

Benzyl chloride was treated with (Me₃Si)₃CLi to give (Me₃Si)₃CCH₂Ph (1). A new styrene derivative, (Me₃Si)₃CCH₂C₆H ₄(CHCH₂-p) (2), was

Full text of DOI:10.1016/j.jorganchem.2004.08.032

Journal of Organometallic Chemistry 690 (2005) 79–83
www.elsevier.com/locate/jorganchem
Synthesis and reactions of p-vinylbenzyltris(trimethylsilyl)methane
*
Kazem D. Safa , Mirzaagha Babazadeh
Organic Chemistry, Faculty of Chemistry, University of Tabriz, 51664 Tabriz, Iran
Received 22 June 2004; accepted 22 August 2004
Available online 30 September 2004
Abstract
Benzyl chloride was treated with (Me3Si)3CLi to give (Me3Si)3CCH2Ph (1). A new styrene derivative, (Me3Si)3CCH2
C6H4(CH@CH2-p) (2), was synthesized by reaction of p-vinylbenzyl chloride with (Me3Si)3CLi in the presence of CuCl. Addition
and oxidation reactions on 2 gave a series of new compounds (Me3Si)3CCH2C6H4X-p (X = CH2CH3, CHBrCH2Br, CHClCH2I,
CHBrCH2I, cyclo-C3H3Cl2, CHOHCH2OH, COOH, CH2OH).
Ó 2004 Elsevier B.V. All rights reserved.
Keywords: Vinylbenzyl chloride; Steric hindrance; Trisyl
1. Introduction
We now describe the preparation of a new organosilyl
styrene derivative, bearing the Tsi ligand, and its reac-
tions with various chemical reagents for the preparation
of some new organosilicon compounds.
p-Vinylbenzyl chloride (VBC), or 4-chloromethylsty-
rene (CMS), is one of the most important monomers
which is produced industrially in pure form. Many
nucleophilic substitutions are possible at the benzylic
chlorine, leaving the double bond unchanged and pro-
viding new functionalized monomers under appropriate
conditions [1–5].
The tris(trimethylsilyl)methyl group, {(Me3Si)3C–}, is
a highly sterically hindered ligand in which three organ-
osilyl groups are bound to the central carbon. It is often
referred to as the ÔtrisylÕ ligand and commonly denoted
by ÔTsiÕ. This ligand has been used extensively as bulky
alkyl substituent in main group, alkali metal, transition
metal and lanthanide chemistry. A large number of me-
tal compounds containing the bulky (Me3Si)3C– group
have been studied [6–13], but there are few references
in the literature about the attachment of the trisyl group
to carbon.
2. Results and discussion
Because of the reactivity of benzylic chlorine, nucleo-
philic substitution reactions on VBC are generally easy
and leave the carbon–carbon double bond unchanged
when the experimental conditions are carefully chosen.
A solvent is necessary, and the duration of the reaction
must be as short as possible with a minimum heating
and with polymerization inhibitor. Many substitution
reactions on VBC have already been performed with
various nucleophiles and new compounds with numer-
ous applications have been obtained [14–16].
2.1. Synthesis of TsiCH2C6H4(CH@CH2-p) (2)
The yield of trisyl substitution on VBC depends on
the temperature and it is increased with increasing tem-
perature. Reaction of VBC with TsiLi in the absence of
an inhibitor under reflux in THF gave an insoluble
*
Corresponding author. Tel.: +98 411 3393076; fax: +98 411
3340191.
E-mail address: dsafa@tabrizu.ac.ir (K.D. Safa).
0022-328X/$ - see front matter Ó 2004 Elsevier B.V. All rights reserved.
doi:10.1016/j.jorganchem.2004.08.032

80
K.D. Safa, M. Babazadeh / Journal of Organometallic Chemistry 690 (2005) 79–83
+
CH CH2 I
CH = CH2
ClCH CH I
2
CH = CH2
(Me Si) CLi +
ClCH2
3
3
_
Cl
I
Cl
+
CuCl / THF
reflux
(Me3Si) CCH2
(Me3Si) CCH2
(Me3Si) CCH2
3
3
3
(5)
(2)
CH = CH2
(Me3Si)3CCH2
Scheme 2.
(2)
Scheme 1.
Scheme 3.
polymer. Therefore, as shown in Scheme 1, a small
amount of CuCl was added as an inhibitor for double
bond polymerization and after heating under reflux for
about 3 h, the expected 2 was obtained in good yield.
12 reacts with chloroform to give the trichloromethyl
anion, which eliminates chloride ion to give dichlorocar-
bene, :CCl2, and 11. This dichlorocarbene added to the
carbon–carbon double bond of 2 to give addition
product 7.
2.2. Miscellaneous reactions of 2
A dilute solution of KMnO4 reacted with 2 to give the
1,2-diol TsiCH2C6H4(CHOHCH2OH-p) (8). KMnO4 is
also the preferred reagent for the oxidative cleavage of
carbon–carbon double bonds [17]. An alternative ap-
proach involves the use of phase transfer reagent to sol-
ubilize permanganate ion in organic solvents [18].
Tributylammonium iodide was used as the phase trans-
fer agent because it is inexpensive and readily available.
Treatment of 2 with KMnO4 in the presence of the
phase transfer agent in acidic medium led to oxidation
and cleavage of the carbon–carbon double bond of 2
to give TsiCH2C6H4(COOH-p) (9). The acidic medium
is used to neutralize hydroxide ions formed during the
reduction of permanganate. In the absence of acid the
accumulation of base promotes side reactions and in-
The new compound 2 is an unsymmetrical alkene and
reacts with electrophilic and oxidizing reagents. The
reaction of 2 with an excess of LiAlH4 in THF gave
the TsiCH2C6H4(CH2CH3-p) (3). Treatment of 2 with
electrophilic addition reagents such as Br2, ICl and IBr
gave addition products TsiCH2C6H4(CHBrCH2Br-p)
(4), TsiCH2C6H4(CHClCH2I-p) (5) and TsiCH2C6H4-
(CHBrCH2I-p) (6), respectively. In the addition of ICl
and IBr to the carbon–carbon double bond, the iodide
atom with lower electronegativity is attached to the
sp2 carbon to give stable benzylic carbocation (Scheme
2), in which the positive charge is delocalized into the
aromatic ring.
Compound 2 also reacted with dichlorocarbene gen-
erated from the reaction of chloroform with 50% aque-
ous NaOH in the presence of a catalytic amount of the
quaternary ammonium salt [Et3(PhCH2)N]Cl to give
TsiCH2C6H4(cyclo-C3H3Cl2-p) (7) as a cyclopropane
derivative of 2. As shown in Scheme 3, both benzyltri-
ethylammonium chloride (11) and benzyltriethylammo-
nium hydroxide (12) partition between the aqueous
and organic phases. In the aqueous phase, 11 reacts with
concentrated hydroxide to give 12. In the organic phase,
Table 1
(Me3Si)3CCH2C6H4X-p
Compound
X
Compound
X
1
2
3
4
5
H
6
CHBrCH2I
cyclo-C3H3Cl2
CHOHCH2OH
COOH
CH@CH2
CH2CH3
CHBrCH2Br
CHClCH2I
7
8
9
10
CH2OH

K.D. Safa, M. Babazadeh / Journal of Organometallic Chemistry 690 (2005) 79–83
81
crease the stickiness of the manganese (IV) oxides, which
precipitate as the reaction proceeds. Compound 9 was
reduced to the related alcohol TsiCH2C6H4(CH2OH-p)
(10) by LiAlH4 in THF (see Table 1).
funnel under dried argon. A mixture of VBC (1.7 g, 10
mmol) and CuCl (0.1 g, 0.99 mmol) in THF (20 ml)
was stirred in an ice bath at 0 to ꢀ5 °C. The solution
of TsiLi in THF was added dropwise over a period of
30 min and the reaction mixture was stirred for about
1 h, and then heated under reflux for 3 h. Then aqueous
NH4Cl was added and the organic layer extracted with
Et2O (50 ml). The ethereal layer was dried with anhy-
drous Na2SO4 and filtered. The solid, obtained by evap-
oration of Et2O from the filtrate, was washed several
times with cold ethanol to give 2 (60%); m.p. 139 °C.
FT-IR (KBr, cmꢀ1) 3066, 3033 (@C–H), 2950, 2890
(C–H aliphatic), 1637 (C@C vinyl), 1605, 1470 (C@C
aromatic), 1250 (C–Si). 1H NMR (CDCl3) 0.11 (s,
27H, Tsi), 3.16 (s, 2H, CH2–Tsi), 5.24 and 5.79 (d, 2H,
@CH2), 6.72 (q, 1H, @CH), 7.39–7.49 (q, 4H, aryl-H).
13C NMR (CDCl3) 3.35 (9C, CH3–Si), 9.88 (1C, C–
SiMe3), 34.52 (1C, CH2–Tsi), 112.75 (1C, @CH2),
135.60 (1C, @CH), 125.56, 127.18, 135.90, 141.41 (6C,
aromatic carbons). m/z (EI): 349 (2%, M+), 334 (5%,
[M–Me]+), 117 (50%, [M–Tsi]+), 91 (35%, C6H5CHþ2 ),
73 (100%, Me3Si+). Anal. Calc. for C19H36Si3 Calc.: C,
65.4; H, 10.3. Found: C, 65.3; H, 10.2%.
3. Experimental
Reactions involving lithium metal, organolithium
reagents and LiAlH4 were carried out under dry argon
to exclude oxygen and moisture from the reaction sys-
tems. Solvents were dried by standard methods.
3.1. Spectra
The Infrared spectra were recorded on a Bruker Spec-
trometer Tensor 27 FTIR with KBr pellets, and 1H
NMR and 13C NMR spectra were run on a Bruker
400 MHz spectrometer at room temperature using
CDCl3 as a solvent. Mass spectra were obtained by
use of a Shimadzu Qp 100X spectrometer at 70 eV.
Elemental analyses were carried out with a Heareus
CHN-ORAPID instrument. Melting points were deter-
mined on a 9100 Electrothermal apparatus.
3.4. Preparation of TsiCH2C6H4(C2H5-p) (3)
3.2. Preparartion of TsiCH2C6H5 (1)
LiAlH4 (5 g, 0.13 mol) was gradually added to a stir-
red solution of 2 (2.0 g, 5.7 mmol) in dry THF (75 ml).
The mixture was heated under reflux for 5 days. Aque-
ous saturated NH4Cl solution was slowly added at
0 °C, and the mixture was extracted with Et2O. The ex-
tract was dried (Na2SO4), and filtered and solvent was
evaporated. The residue was then recrystallized from
A solution of TsiH (1.56 g, 6.8 mmol) in THF (15 ml)
reacted with MeLi generated from MeI (1.25 g, 8.8
mmol) and Li (0.12 g, 17.6 mmol) in Et2O (10 ml). After
the lithiation of TsiH was complete [13], a solution of
benzyl chloride (0.576 g, 4.5 mmol) in THF (25 ml)
was added dropwise with stirring to solution of the flask
at room temperature. The mixture was heated under re-
flux for about 2 h, poured into aqueous NH4Cl and ex-
tracted with Et2O. The extract was dried with anhydrous
Na2SO4, filtered and solvent evaporated. The residue
was recrystallized from methanol to give 1 (78%); m.p.
81 °C. FTIR (KBr, cmꢀ1) 3060 (C–H aromatic), 2960,
2910 (C–H aliphatic), 1600, 1470 (C@C aromatic),
1
EtOH to give 3 (94%); m.p. 132 °C. H NMR (CDCl3)
0.11 (s, 27H, Tsi), 1.26 (t, 3H, CH3), 2.55 (q, 2H,
CH2–Me), 3.19 (s, 2H, CH2–Tsi), 7.33–7.40 (q, 4H,
aryl-H). 13C NMR (CDCl3) 2.07 (9C, CH3–Si), 9.80
(1C, C–SiMe3), 17.08 (1C, CH3), 28.26 (1C, CH2–Me),
34.55 (1C, CH2–Tsi), 126.19, 128.08, 141.90, 149.94
(6C, aromatic carbons). m/z (EI): 350 (5%, M+), 335
(63%, [M–Me]+), 321 (18%, [M–Et]+), 119 (16%, [M–
Tsi]+), 105 (60%), 91 (72%), 73 (100%). Anal. Calc. for
C19H38Si3: C, 65.0; H, 10.9. Found: C, 65.0; H, 10.7%.
1
1250 (Si–C). H NMR (CDCl3) 0.11 (s, 27H, Tsi), 3.18
(s, 2H, CH2–Tsi), 7.18–7.31 (m, 5H, aryl-H). 13C
NMR (CDCl3) 3.4 (9C, CH3–Si), 10.7 (1C, C–SiMe3),
35.7 (1C, CH2–Tsi), 126.24, 127.95, 130.60, 142.56
(6C, aromatic carbons). m/z (EI): 323 (2%, M+), 308
(10%, [M–Me]+), 235 (25%, [M–Me4Si]+), 162 (50%,
[M–Me3Si–Me4Si]+), 135 (55%, Me2PhSi+), 91 (10%,
C6H5CHþ2 ), 73 (100%, Me3Si+). Anal. Calc. for
C17H34Si3: C, 63.3; H, 10.5. Found: C, 62.9; H, 10.6%.
3.5. Preparation of TsiCH2C6H4(CHBrCH2Br-p) (4)
A solution of Br2 (0.16 g, 1 mmol) in CCl4 (15 ml)
was added dropwise during a period of 30 min with stir-
ring to a solution of 2 (0.2 g, 0.57 mmol) in CCl4 (5 ml)
at 0 °C. The mixture was stirred for 1 h at room temper-
ature, then solvent was removed under reduced pressure
and the residue recrystallized from EtOH to give 4
3.3. Preparation of TsiCH2C6H4(CH@CH2-p) (2)
1
A solution of TsiLi that had been made by the reac-
tion of TsiH (4.6 g, 20 mmol) in THF (30 ml) with MeLi
generated from MeI (3.54 g, 25 mmol) and Li (0.35 g, 50
mmol) in Et2O (15 ml) was transferred into a dropping
(91%); m.p.>152 °C. H NMR (CDCl3) 0.12 (s, 27H,
Tsi), 3.18 (s, 2H, CH2–Tsi), 4.01(m, 2H, CH2Br), 5.11
(q, 1H, CHBr), 7.21–7.30 (q, 4H, aryl-H). 13C NMR
(CDCl3) 2.06 (9C, CH3–Si), 10.06 (1C, C–SiMe3),

82
K.D. Safa, M. Babazadeh / Journal of Organometallic Chemistry 690 (2005) 79–83
33.52 (1C, CH2–Tsi), 34.12 (1C, CH2Br), 49.47 (1C,
CHBr), 126.19, 127.08, 134.57, 148.57 (6C, aromatic
carbons). m/z (EI): 508 (2%, M+), 493 (9%, [M–Me]+),
414 (19%, [M–Br–Me]+), 341 (15%, [M–Br–Me4Si]+),
289 (47%), 277 (60%), 269 (35%), 198 (52%), 137
(67%), 91 (35%), 73 (100%). Anal. Calc. for
C19H36Si3Br2: C, 44.8; H, 7.1. Found: C, 44.6; H, 7.0%.
ml). The organic layer was separated and the aqueous
phase extracted with Et2O (25 ml). The organic fractions
were combined and washed once with water (20 ml). The
cloudy organic layer was dried with Na2SO4, filtered and
solvent evaporated. The residue was purified by prepar-
ative TLC (silica gel, 1:1 cyclohexane:dichloromethane
as eluent) to give 7 (75%); m.p.>124 °C. 1H NMR
(CDCl3) 0.10 (s, 27H, Tsi), 1.96 (q, 2H, CH2–CCl2),
2.95 (t, 1H, CH–CCl2), 3.18 (s, 2H, CH2–Tsi), 7.46–
7.69 (q, 4H, aryl-H). 13C NMR (CDCl3) 2.44 (9C,
CH3–Si), 10.07 (1C, C–SiMe3), 27.94 (1C, CH2–cyclo-
propyl), 33.74 (1C, CH–cyclopropyl), 35.15 (1C, CH2–
Tsi), 64.34 (1C, CCl2), 126.38, 130.20, 135.38, 148.45
(6C, aromatic carbons). m/z (EI): 432 (2%, M+), 417
(4%, [M–Me]+), 382 (36%, [M–Me–Cl]+), 346 (42%,
[M–Me–Cl2]+), 307 (61%, [M–Me–C3H3Cl2]+), 234
(41%), 161 (22%), 105 (24%), 73 (100%). Anal. Calc.
for C20H36Si3Cl2: C, 55.6; H, 8.4. Found: C, 55.4; H,
8.6%.
3.6. Preparation of TsiCH2C6H4(CHClCH2I-p) (5)
A solution of ICl (0.16 g, 1 mmol) in CCl4 (15 ml) was
added dropwise to a stirred solution of 2 (0.2 g, 0.57
mmol) in CCl4 (5 ml). The mixture was stirred for 1 h
and the solvent removed under reduced pressure. The
residue was recrystallized from EtOH to give 5 (92%);
m.p. 162 °C. 1H NMR (CDCl3) 0.11 (s, 27H, Tsi),
3.16 (s, 2H, CH2–Tsi), 3.95 (m, 2H, CH2I), 5.19 (t,
1H, CHCl), 7.26–7.38 (q, 4H, aryl-H). 13C NMR
(CDCl3) 2.44 (9C, CH3–Si), 10.01 (1C, C–SiMe3),
14.06 (1C, CH2I), 35.14 (1C, CH2–Tsi), 61.93 (1C,
CHCl), 124.88, 130.20, 135.01, 147.38 (6C, aromatic car-
bons). m/z (EI): 511 (3%, M+), 496 (6%, [M–Me]+), 384
(40%, [M–I]+), 369 (25%, [M–I–Me]+), 354 (12%, [M–I–
Me4Si]+), 280 (32%), 224 (41%), 153 (42%), 91 (15%), 73
(100%). Anal. Calc. for C19H36Si3ICl: C, 44.6; H, 7.1.
Found: C, 44.4; H, 7.0%.
3.9. Preparation of TsiCH2C6H4(CHOHCH2OH-p) (8)
A solution of 1% KMNO4 in acetone was added
dropwise to a stirred solution of 2 (0.2 g, 0.57 mmol)
in CH2Cl2 (15 ml) at 0 °C. The colour immediately be-
came dark brown. The mixture was stirred at 0 °C for
about 1 h, then water (25 ml) was added. The organic
layer was extracted with Et2O, and the extract was dried
by anhydrous Na2SO4 and filtered and solvent evapo-
rated. The residue was recrystallized from EtOH and
purified by preparative TLC (silica gel, 1:2 n-hex-
ane:dichloromethane as eluent) to give 8 (68%); m.p.
186 °C. FTIR (KBr, cmꢀ1) 3350 (O–H), 1250 (C–Si),
1100, 1050 (C–O). 1H NMR (CDCl3) 0.10 (s, 27H,
Tsi), 3.22 (s, 2H, CH2–Tsi), 3.52 (s, 2H, OH), 4.29 (m,
2H, CH2–O), 4.46 (q, 1H, CH–O), 7.43–7.81 (q, 4H,
aryl-H). 13C NMR (CDCl3) 2.44 (9C, CH3–Si), 9.95
(1C, C–SiMe3), 35.15 (1C, CH2–Tsi), 64.33 (1C,
CH2OH), 126.38, 130.20, 137.07, 148.22 (6C, aromatic
carbons). m/z (EI): 382 (2%, M+), 381 (20%, [M–H]+),
350 (58%, [M–Me–OH]+), 277 (37%, [M–OH–Me4Si]+),
260 (45%), 187 (54%), 145 (20%), 73 (100%). Anal. Calc.
for C19H38Si3O2: C, 59.6; H, 10.1. Found: C, 59.4; H,
9.7%.
3.7. Preparation of TsiCH2C6H4(CHBrCH2I-p) (6)
A solution of IBr (0.2 g, 1 mmol) in CCl4 (15 ml) was
added dropwise with stirring to a solution of 2 (0.2 g,
0.57 mmol) in CCl4 (5 ml). The mixture was stirred for
1 h and the solvent removed under reduced pressure.
The solid residue was recrystallized from EtOH to give
1
6 (87%); m.p. 170 °C. H NMR (CDCl3) 0.11 (s, 27H,
Tsi), 3.18 (s, 2H, CH2–Tsi), 3.86 (m, 2H, CH2I), 4.92
(t, 1H, CHBr), 7.25–7.41 (q, 4H, aryl-H). 13C NMR
(CDCl3) 2.45 (9C, CH3–Si), 9.88 (1C, C–SiMe3), 17.77
(1C, CH2I), 34.52 (1C, CH2–Tsi), 55.95 (1C, CHBr),
124.76, 127.48, 135.55, 147.51 (6C, aromatic carbons).
m/z (EI): 555 (2%, M+), 428 (2%, [M–I]+), 413 (15%,
[M–I–Me]+), 340 (16%, [M–I–Me4Si]+), 267 (30%), 197
(30%), 91 (15%), 73 (100%). Anal. Calc. for
C19H36Si3IBr: C, 41.0; H, 6.5. Found: C, 40.9; H, 6.6%.
3.8. Preparation of TsiCH2C6H4(cyclo-C3H3Cl2-p) (7)
3.10. Preparation of TsiCH2C6H4(COOH-p) (9)
To a mixture of 2 (2.0 g, 5.7 mmol), CHCl3 (3.2 g, 27
mmol), 50% aqueous NaOH (20 ml) and CH2Cl2 (20 ml)
was added [Et3(CH2Ph)N]Cl (0.2 g). The mixture was
stirred vigorously to give a thick emulsion. The temper-
ature was gradually raised to 40 °C and then kept be-
tween 40–45 °C by cooling with an ice bath. After the
exothermic reaction was complete (about 1 h), the dark
brown reaction mixture was heated to 55–60 °C for 1 h.
Then allowed to cool to 30 °C and diluted with water (50
KMnO4 (5.0 g, 34 mmol) was added in small portions
over 1 h to a rapidly stirred solution of distilled water
(50 ml), 9 M sulfuric acid (10 ml), (n-Bu)4NI (0.5 g), gla-
cial acetic acid (5 ml), CH2Cl2 (50 ml) and 2 (3.0 g, 8.5
mmol) and stirring was continued for an additional 18 h
at room temperature. The organic layer was separated
and the aqueous layer extracted with two 50 ml portions
of CH2Cl2. The organic extracts were combined, washed
with two 50-ml portions of water, dried with anhydrous

K.D. Safa, M. Babazadeh / Journal of Organometallic Chemistry 690 (2005) 79–83
83
Na2SO4 and filtered. After evaporation of CH2Cl2, the
yellowish residue was recrystallized from a mixture of
ethanol and water (8:2 v:v) to give 9 (83%); m.p. 159
°C. FTIR (KBr, cmꢀ1) 3328 (O–H), 1687 (C@O), 1290
Me–OH]+), 307 (19%, [M–Me–CH2OH]+), 234 (20%),
161 (25%), 105 (27%), 91 (40%), 73 (100%). Anal. Calc.
for C18H36OSi3: C, 61.3; H, 10.3. Found: C, 60.8; H,
9.8%.
1
(C–O), 1250 (C–Si). H NMR (CDCl3) 0.11 (s, 27H,
Tsi), 3.16 (s, 2H, CH2–Tsi), 7.39–7.49 (q, 4H, aryl-H),
11.2 (s, 1H, COOH). 13C NMR (CDCl3) 2.44 (9C,
CH3–Si), 10.12 (1C, C–SiMe3), 35.15 (1C, CH2–Tsi),
126.38, 127.28, 130.21, 150.00 (6C, aromatic carbons),
166.83 (1C, COOH). m/z (EI): 367 (4%, M+), 352
(62%, [M–Me]+), 335 (83%, [M–Me–OH]+), 322 (20%,
[M–COOH]+), 307 (19%, [M–Me–COOH]+), 278
(40%), 261 (38%), 189 (25%), 165 (35%), 91 (24%), 73
(100%). Anal. Calc. for C18H34Si3O2: C, 58.9; H, 9.3.
Found: C, 59.0; H, 9.7%.
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A mixture of 9 (0.5 g, 1.37 mmol) and LiAlH4 (1.0 g,
26 mmol) in dry THF (50 ml) was stirred and heated un-
der reflux for 24 h. The mixture was allowed to cool,
then carefully treated with aqueous saturated NH4Cl
and extracted with Et2O. The extract was dried
(Na2SO4), filtered and solvent evaporated, and the resi-
due was recrystallized from EtOH to give 10 (87%); m.p.
142 °C. 1H NMR (CDCl3) 0.10 (s, 27H, Tsi), 2.35 (s, 1H,
O–H), 3.18 (s, 2H, CH2–Tsi), 4.46 (s, 2H, CH2O), 7.24–
7.32 (q, 4H, aryl-H). 13C NMR (CDCl3) 2.48 (9C, CH3–
Si), 10.02 (1C, C–SiMe3), 35.15 (1C, CH2–Tsi), 64.33
(1C, CH2OH), 126.38, 130.22, 137.57, 146.17 (6C, aro-
matic carbons). m/z (EI): 353 (1%, M+), 338 (40%,
[M–Me]+), 337 (28%, [M–Me–H]+), 321 (18%, [M–
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