The kinetics of methanolysis (solvolysis) in 97.4% MeOH-dioxan of a series of 4′-substituted 4-benzyloxybenzyl chlorides, and of 4-anisyl, 4-phenoxybenzyl, and benzyl chlorides have been studied and discussed, including comparisons with the data for the corresponding series of benzoyl chlorides, previously reported by us. The 4′-substituted precursor alcohols, chlorides, and product methyl ethers are all new compounds. 4-Anisyl chloride and the series of benzyloxybenzyl chlorides react by the SN1 mechanism, whereas benzyl chloride reacts by the SN2 mechanism. 4-Phenoxybenzyl chloride shows intermediate behaviour. A similar pattern was observed with the corresponding benzoyl compounds. In both series the reactivity order is CH3O &gt; 4′-CH3C6H 4CH2O (-0.76) &gt;C5H5CH 2O (-0.74) &gt; 4′-ClC6H4CH2O (-0.69) &gt; 4′-NO2C6H4CH2O (-0.60) &gt; C6H5O &gt; H (values in parentheses are new σ+ values). At 25° the overall range of rates is 4 290 in the benzyl series, compared with only 2.42 in the benzyl series. The Arrhenius parameters in the two series demonstrate, however, an underlying similarity with obvious differences superimposed. In both series, the introduction of 4-OR groups leads to a ΔS‡ increase of ca. 40 J mol-1 K -1. In the benzyl series this is accompanied by ΔE‡ decreases of ca. 6-10 kJ mol-1, whereas in the benzoyl series ΔE‡ values increase by ca. 10-15 kJ mol-1. The equation log k = log k0 + n[MeOH] in mixtures with increasing content of dioxan, was used to study the rate dependence on MeOH concentration. Values of n are ca. 5 between 97.4 and 8.3.% MeOH, and ca. 3 between 83.3 and 50.0% MeOH.110010

Jorge J.A.L.

Kiyan N.Z.

Miller J.

Miyata Y.

English

Repositorio da Producao Cientifica e Intelectual da Unicamp

100 J.C.S. Perkin 11 
Methanolysis (Solvolysis) and Synthesis of 4'-Substituted 4-Benzyloxy- 
benzyl Chlorides and Some Related Compounds : Comparisons with the 
Corresponding Benzoyl Compounds 
By Jorge Armando Luis Jorge, Nilo Zengo Kiyan, and Yukino Miyata, lnstituto do Quimica, Universidade de 
Joseph Miller," lnstituto de Quimica, Universidade Estadual de Campinas, Caixa Postal 11 70, 13.1 00 Cam- 
SBo Paulo, Caixa Postal 20.780,Ol .OOO SBo Paulo SP, Brasil 
pinas SP, Brasil 
The kinetics of methanolysis (solvolysis) in 97.4% MeOH-dioxan of a series of 4'-substituted 4-benzyloxybenzyl 
chlorides, and of 4-anisy1, 4-phenoxybenzy1, and benzyl chlorides have been studied and discussed, including 
comparisons with the data for the corresponding series of benzoyl chlorides, previously reported by us. The 4'- 
substituted precursor alcohols, chlorides, and product methyl ethers are a l l  new compounds. 4-Anisyl chloride 
and the series of benzyloxybenzyl chlorides react by the S,1 mechanism, whereas benzyl chloride reacts by the S,2 
mechanism. 4- Phenoxybenzyl chloride shows intermediate behaviour. A similar pattern was observed with the 
corresponding benzoyl compounds. In both series the reactivity order is CH,O > 4'-CH,C,H4CH,0 (-0.76) 
>C,H5CH,0 (-0.74) 7 4'-CIC,H4CH20 (-0.69) > 4'-N02C,H4CH,0 (-0.60) > C6H50 > H (values in 
parentheses are new IS+ values). At 25" the overall range of rates is 4 290 in the benzyl series, compared with only 
2.42 in the benzyl series. The Arrhenius parameters in the two series demonstrate, however, an underlying simil- 
arity with obvious differences superimposed. In both series, the introduction of 4-OR groups leads to a A S  
increase of ca. 40 J mol- l  K- l .  In the benzyl series this is accompanied by A€$ decreases of ca. 6-10 kJ mol-l, 
whereas in the benzoyl series A€% valuesincrease by ca. 10-1 5 kJ mol- l. The equation log k = log k, + n[MeOH] 
in mixtures with increasing content of dioxan, was used to study the rate dependence on MeOH concentration. 
Values of n are ca. 5 between 97.4 and 8.3.% MeOH, and ca. 3 between 83.3 and 50.0% MeOH. 
FOLLOWING studies of the methanolysis (solvolysis) in 
97.4% MeOH-dioxan of 4'-substituted 4-benzyloxy- 
benzoyl chlorides and some related compounds, we have 
studied the same reaction with the corresponding benzyl 
chlorides, to demonstrate the shift from SN2 to SN1 
mechanism and the similarities and differences in the 
kinetic data. 
All the 4'-substituted chlorides, their precursor 
alcohols, and product methyl ethers are new compounds. 
EXPERIMENTAL 
Materials.-The 4'-substituted-4-benzyloxybenzyl alco- 
hols, from which we prepared the chlorides, were synthesized 
by two methods. Method A involved the condensation of 
4-hydroxybenzyl alcohol with various benzyl chlorides or 
bromides in alkaline r n e d i ~ r n . ~  Method B involved the 
reduction of the corresponding methoxycarbonyl com- 
pound with lithium aluminium hydride.* 
4-Hydroxybenzyl alcohol was obtained by reduction of 
4-hydroxybenzaldehyde with sodium borohyd ride in aqueous 
1. 1N-NaOH.2 4-Chlorobenzyl bromide was prepared by the 
side-chain bromination (Br, ; reflux) of purified 4-chlorotolu- 
ene irradiated with light.5 4-Nitrobenzyl chloride was pre- 
pared by the nitration of purified. benzyl chloride, using 
concentrated HNO, and H,SO, under reflux., 4-Anisyl 
chloride was prepared by treating 4-anisyl alcohol with 
SOCl, in light petroleum (b.p. 65-110 "C), followed by 
fractional distillation at. reduced pressure; as well as by 
treating 4-anisyl alcohol with concentrated HCl, followed 
by fractional distillation in a Kugelrohr apparatus at reduced 
p r e s ~ u r e . ~  4-Methylbenzyl chloride was prepared by thc 
chloromethylation of toluene with paraformaldehyde, 
ZnCl,, and HC1 (gas).8 
The 4'-su bstituted 4-benzyloxybenzyl alcohols produced 
by Method A were converted into the corresponding chlorides 
by reaction with SOC1, in light petroleum (b.p 65-1 10 "C). 
The methoxycarbonyl compounds required for Method B 
were prepared as previously described by  US.^ The reduc- 
tion to  the corresponding alcohols was effected by lithium 
aluminium hydride in anhydrous t e t r ahydr~fu ran .~  
9-Phenoxybenzyl chloride was prepared by the chloro- 
methylation of diphenyl ether, using formaldehyde (30% 
aqueous) and HC1 (concentrated and gas) in a modification 
of literature p ro~edures .~ - l~  An alternative preparation via 
the reduction of p-phenoxybenzoyl chloride l2  involved the 
sequence : diphenyl ether 4-bromodiphenyl ether, 
conversion of Br into COCl via the MgBr compound, and its 
reaction with CO, to give the acid, which was treated with 
SOCl,. 
TABLE 1
4'-Substituted 4-benzyloxybenzyl alcohols,* chlorides,* and methyl ethers * 
4'-Substituent Preparation Yield (%) M.p. ('C? Yield (xi M.p. ( O G  M.p. ("C) 
Methyl 
A ethers 
Alcohol a Chloride a 
r r--- 
H Methods A,B 70, 76 87-88 70 78,5-80 
NO, 
c1 
CH, 
OCH, 
Method A 50 b 126- 128 51 86-87 67-69 
Method B 72 103-104,5 60 99-101 51-63 
Method B 59 105-106,5 64 7 4 7 5  59,5-61 
Method B 61 115-117 t 
* All are new compounds except the parent (unsubstituted) alcohol, chloride, and methyl ether. 
8 From light petroleum (b.p. 65-110 "C). 
t Not obtained at  purity (> 99% 
From EtO H-H,O 
suitable for kinetic studies. 
From MeOH-H,O then light petroleum. From MeOH-H,O. 
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€98 1 101 
TABLE 2
Experimental rate constants * for niethanolysis (solvolysis) of fi-XC,H,CH,Cl in 97.4% MeOH-ilioxan (except as 
shown). Solutions 2.35 x lop3 R.I 
1 OQK/s-l ( t /"C) 104 ~ l S - 1  p/oc) 
X (temp. in parentheses) X (temp. in parentheses) 
I'h 0 0.321, 0.383 (41.0) p-NOzC,H4CH2O 1.04, 1.04 (33.0) 
1.49, 1.52, 1.52 (57.0) 5.69, 5.72, 5.80 (49.0) 
2.95 (65.0) 12.9, 12.9 (57.0) 
M e 0  1.05, 1.06, 1.07, 1.07 (17.0) p-ClC,H ,CH 2O 1.02, 1.02 (25.0) 
0.700, 0.713, 0.713 (49.0) 2.49, 2.50, 2.56, 2.56 (41.0) 
2.76, 2.81 (25.0) 2.66, 2.66, 2.66, 2.67 (33.0) 
6.52, 6.57 (33.0) 6.28, 6.28, 6.33, 6.43 (41.0) 
15.5, 15.8, 16.0 (41.0) 14.6, 14.7, 14.7, 14.8 (49.0) 
34.3, 35.2 (49.0) 
P-CH3C6H4CH20 2.20, 2.23 (25.0) 
0.713 (17.0) 5.64, 5. 65,5.67, 5.68 (33.0) 
1.80, 1.83 (25.0) 13.4, 13.4, 13.4 (41.0) 
4.33, 4.35, 4.38 (33.0) 28.8, 28.9, 29.0, 29.0 (49.0) 
10.1, 10.1, 10.1, 10.2 (41.0) 
5.78 (83.3% MeOH) (41.0) 
3.30 (70.0% MeOH) (41.0) 
1.52 (50.0% MeOH) (41.0) 
* In accordance with the high level of reproducibility, the percentage errors are alniost all < 3 lye, and correlation cwfticients 
almost all in the range 0.9990--1.0000. 
l'hCH,(_) 
The structures and purity of all the conipoiinds and the 
product methyl ethers (see Table 1) were confirmed by 
elemental analysis, i.r., n.m.r., and mass spectra) as well as 
by titrimetric or gravimetric estimation of the chlorine after 
displacement to form chloride ion. KO compound was 
< 99% pure by chloride analysis. For this reason we do not 
yet report kinetic results for tlic 4'-methoxy-compound 
which we have so far been unable to purify to this level. 
Kinetic Studies.-With a Metrohm conductance bridge 
E382 we used a conductimetric method t o  obtain rate 
constants, viz.  by Guggenlieim plot analysis of the con- 
ductance increases resulting from the niethanolysis of ca. 
2 .3  Y lW31\1 solutions o f  the various chlorides in 97.4% 
RIeOH-2.6% dioxan : the small amount of dioxan, which 
has little effect on rates, was added to increase the solvent 
power of the medium. Sonic measurements were also made 
in mixtures containing 83.3,  70.0, and 50.0yo MeOH with 
dioxan. 
Rate constants and derived parameters evaluated by a 
PDP 10 computer are given in Tables 2 and 3. 
1)iscussIoN 
The phenyl group facilitates the Ss2 a5 well as the 
S N l  mechanism.13 The level of the former is diminished 
and of the latter augmented by electron-donating groups 
( e g .  4-OMe) in the ring. Thus benzyl chloride reacts in 
rnost conditions by the SN2 and p-anisyl chloride by the 
S N 1  mechanism.l* 
Table 3, which includes some literature data, demon- 
strates the marked differences in the patterns of rates and 
Arrhenius parameters of benzyl chloride when com- 
pared with 4-anisyl and the various 4'-substituted 4- 
Senzyloxybenzyl chlorides. The intermediate character 
of kinetic data for 4-phenoxybenzyl chloride is also clear. 
Our results demonstrate that  the 4-OR groups cause a 
2 800-4 300-fold increase in solvolysis rates (26 "C), a 
change in the order of dependence on methanol con- 
centration in mixtures with dioxan, and marked changes 
in the pattern of Arrhenius parameters. 
Analysis of the latter shows that the rate increases 
relate mainly to substantial increases (less negative) of 
the entropy of activation ( A S )  of ca. 40 J mol-I K-l, 
which is equivalent to a log ,,A increase from cu. 9 to 1 1 .  
We relate these increases to the looser transition-state 
implied by the shift from the S N 2  to the S x l  mechanism. 
I t  is noteworthy that the AS: (and log,,/!) values for 
benzyl chloride are themselves quite high, which we 
regard as implying an SN1-like reaction even in that case. 
Activation energy decreases of the order of 6-10 kJ 
TABLE 3
Rate constants and derived kinetic data for nietlianolysis of 4-substituted benzyl chlorides in MeOH-dioxan 97.4% (w/w), 
except as shown 
Rate constant 
105 K / S ~  Relative rates Activation Frequency Activation 
r--hp ?--h.--___ energy factor entropy 
H *  0.006 36 1 .00 94.1 9.3 - 75.1 
PhO 0.597 3.22 93.9 0.032 82.2 9.2 - 77.0 
Me0 27.3 158 4 290 1.56 84.8 11.3 - 36.4 
PhCH20 18.1 101 2 850 1 .oo 84.2 11.2 - 38.3 
Substituent 25.0 "C 41.0 'z 25.0 "C 41 .O '2 h E t / k  Jmol-l log,, (A / sP)  A S /  J m o P  K-1 
In 83.3% MeOH 57.9 0.572 
Jn 70% MeOH 33.0 0.327 
In 50% MeOH 15.2 0.150 
p-NO,C,H4CH,O 4. I3 25.3 649 0.251 87.9 11.0 - 42.6 
p-MeC,H4CH,0 22.8 3 590 1.33 85.1 11.3 - 36.4 
P-CIC,H,CH,O 10.4 1640  0.627 88.1 11.5 -33.0 
* See D. L. Dalrymple et. al., J .  Ovg. Chem., 1964, 29, 2647; R. A. Clement et al., J .  Amer. Chem. SOC., 1960, 82, 2449. 
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102 J.C.S. Perkin II 
mol-’ are ascribed to enhanced conjugation in and sol- 
vation of the forming 4-K0C6H,CH2’ intermediates. 
The relationship log k = log K O  + dJJleOH] was used 
to  evaluate the dependence on methanol concentration, 
in the case of metlianolysis of the parerit tenzyloxybenzyl 
chloride. The N value was ca. 5 between 97.4 and 83.30j0 
methanol, and ca. 3 between 83.3 and 50.00/, methanol. 
These values are consistent with the operation of the SN1 
mechanism, suffering some inhibition as the proportion 
o f  methanol decreases. 
The high precision of the kinetic data is indicated by 
the satisfying relationship of rates within tlie series of 
4’-substitnted 4-benzyloxybenzyl chlorides including 4‘-H 
and in comparing them all with values for 4-anisyl 
chloride. 
Comparing CH,O ant1 ArCH,O groups as h u h -  
stituents, the donating power of oxygen should be less in 
tlie latter, since a C,H, group is electron-withdrawing 
compared to FI when joined to saturated carbon; and its 
effect slmuld be modified by 4‘-substituents in a readily 
underst andable way. Thus we found the reactivity 
order of niethanolysis (solvolysis) of 4-XC6H4CH,C1 to 
CIC,EQ,CH,O > 4’-N02C6H,CH20. The range of rates 
is only cu. &fold and the Arrhenius parameters are 
similar for all the compounds. 
&4pplying the Hammett equation, and using the widely 
accepted \ d u e  for c s + p - ~ 3 1 c  of -0.78 our reaction series 
has i? minimum * Q value of --4.7 (25 “C). We thus 
estimate new opt values (4’-XC6H4CH,0) : 4’-CH, 
Data for the 4’-substituted 4-benzyloxybenzyl clilor- 
ide solvtrlyses permit the evaluation of a subsidiary p’ 
constant using ordinary 0 values for the 4’-substituents. 
The p’ value obtained is -0.82; and the ratio p’ : p is 
equivalent to a transmission coefficient, which has the 
value 0.18. There are no literature values for trans- 
mission across a benzene ring and attached niethylene 
to an oxygen atom, itself exercising a substituent effect 
across a benzene ring to an attached methylene reaction 
centre. Comparison with tlie results given in our earlier 
paper on methanolysis (solvolysis) of the corresponding 
berizoyl clilorides cleInonstrates a number of interesting 
featurcs. However, we first emphasize some differences 
betwvecn the functional groups involved. A COCl 
group has a structure very favourable for the non- 
synchronous atldition-elimination S2..2 mechanism (AE 
be‘ X == CHSO > 4’--CH3C6H4C&O > C6]C-I&H,0 > 4’- 
-0.76, 4’--M --0.?4, 4”CI -0.69, 4’-NO, -0.60. 
SN2). I t  is however also favourable for the S N I  mecli- 
acism, due to the internal stabilisation of the acylium ion. 
The additional conjugation with the phenyl group in 
bcnsoyliurn ion further favours the S N l  and impedes the 
* Minimum value hecausc the S N I  rate for benzyl chloride 
methnnolynis :nust be less than the Sp2 experimental value used 
to  obtain p. 
AE SN2 mechanism. Nevertheless in most conditions 
(including neutral methanolysis) benzoyl c11lu1 ide reacts 
by the latter mechanism but the methanolysis of 4- 
anisoyl and 4-benzyloxybcnzoyl chlorides has marked 
S N l  character. 
Comparisons of kinetic data for the two series demon- 
strate obvious substantial differences superimposed on a 
certain similarity in pattern. The principle difference is 
that  the range of substituents studied by us corresponds 
to a large range of rates in the benzyl series, but a TTery 
much smaller range of rates in the benzoyl series. Never- 
theless the substituent order of rates is the same for both 
4-XC6H,COC1 and 4-XC6H,CH,Cl series, viz.  4-X == 
CH30 > 4’-CH,C6W,CH2O > C6H,CH20 > 4’-C1C6H4- 
CH20 > 4’-N0,C6H,CH20. 
We explain the large differences in relative rates as 
follows. In the COCl reactions tlie CO group itself 
markedly favours the SN1 (as well as the AE S N 2 )  
mechanism, so that substituents in the benzene ring 
joined to tlie COCl group simply modify it. In contrast, 
in the CH,C1 reactions, the CH, group contains no 
element favouring SN1 reactions. I t  is the hemene ring 
joined to it (especially when containing electron-donating 
substituents) which makes the .SKI reactions possible, so 
that substituent effects are much laxger. 
Table 4 illustrates very clearly the difference between 
the two series. 
T A B L E  4 
Substituent rate ratios at 25” of methanolysis (solvolysis 
in 97.47/, iLIeOH-dioxan) of some benzoyl and bcnzyl 
chlorides (hrCOC1 and ,4rCH2C1) 
Reaction centre 
COCl CH,CI 
€I 1 1 
0.895 23.9 
1.29 649 
C6H50 
4’-NC)2C,H4CH,0 
4’-CH,C6H4CH,0 2.15 3 590 
CH,O 2.42 4 290 
Ar group, showing -----A- -\ 
4-X of 4-XC8H4 
C,H5C€120 2.01 2 850 
As interesting as the iarge differences in substituent 
effects is a certain similarity in Arrhenius parameter 
patterns. In  both series, 4-OR groups cause AS1 
increases of the order of 40 J mol-l K-l which we have 
related (see above) to  the marked loosening of the 
transition state in the shift from S N 2  t t h  S K l  reactions. 
I t  is therefore the AEX values which discriminate the two 
series. In  the benzyl series, as we mentioned, A D  
values for the 4-ROC6K4 compounds are ca. 6-10 kJ 
mol-l lower than that of tlie C,H, compound. In the 
benzoyl series the AEI values are ca. 10-15 kJ mol-1 
higher than the value of the C6M, compound. 
We comment that the rate-limiting transition states of 
SN2 reactions (benzoyl series) have a much greater 
degree of bond formation (nucleophile to electrophilic 
carbon) than in the transition-states of synchronous S& 
reactions (benzyl series)” This implies a considerably 
greater loss of bonding energy in the change to an S N ~  
mechanism. The A A E t  values mentioned above are 
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103 
consistent with these comments, as well as the effect of 
' built-in ' conjugation in the benzoyl series. 
I t  is satisfying that  in both series the values of the 
Arrhenius parameters of the 4-phenoxy-compounds have 
intermediate values. As pointed out by Kohnstam l3 
the conjugation of the ether oxygen with two benzene 
rings must considerably reduce its ability to facilitate 
S N ~  reactions, whereas its effect on S N ~  reactions should 
be much less. 
Our final comments are on the absolute values of the 
rates in the benzyl and benzoyl series. The very large 
difference in s N 2  rates is shown by the rate ratio PhCOCl : 
PhCH2C1 for methanolysis in 97.404 MeOH-dioxan, which 
equals 6.75 x lo4. The large difference in the change 
from s ~ 2  to s N 1  reactions is shown by the rate ratios 
for the rnethanolysis (same solvent) of 4-MeOC6H4COC1 :
C1, equal to only 38.1 and 47.7, respectively. 
4-MeOC6H4CH2C1 and 4 BZOC6H4COCl: 4 RZOC6H4CHg- 
[9/1572 Received, 3rd October, 19791 
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Methanolysis (solvolysis) And Synthesis Of 4′'-substituted 4-benzyloxybenzyl Chlorides And Some Related Compounds: Comparisons With The Corresponding Benzoyl Compounds

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Methanolysis (solvolysis) And Synthesis Of 4′'-substituted 4-benzyloxybenzyl Chlorides And Some Related Compounds: Comparisons With The Corresponding Benzoyl Compounds

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