64
H. Roshan, P. Rashidi-Ranjbar / Journal of Molecular Structure 980 (2010) 59–65
O
O
O
O
OH
AlCl3
R
R
OH
HO
HO
HCl / Zn (Hg)
PPA
Al ( Hg )
O
+
R
O
O
R
R
R
4
7a ( R = H )
3a (R = H)
3b (R = CH3)
6a ( R = H )
6b ( R = CH3)
5a ( R = H )
5b ( R = CH3 )
8a ( R = H )
8b ( R = CH3)
7b ( R= CH3)
Cl
Cl
Cl
R
Cl
R
R
R
R
R
NaOH / CHCl3
P.T.C
Cl
Cl
+
+
Cl
Cl
R
R
Cl
Cl
10a ( R= H )
10b ( R = CH3)
9a ( R = H )
9b ( R = CH3)
11a ( R = H )
11b ( R = CH3)
12a ( R = H )
12b ( R = CH3)
R'O
Cl
R'O
Cl
R
Cl
Cl
R'OH
Cl
Cl
Cl
R
Cl
+
R
R
Cl
R
R
Cl
OR'
OR'
OMe
OEt
OMe
OEt
R
H
H
Me
Me
R
H
H
Me
Me
1a
1b
1c
1d
2a
OMe
11a ( R = H )
11b ( R = CH3)
2b
2c
2d
OEt
OMe
OEt
Scheme 3.
(m, 1H), 4.06 (dd, J = 12.22, 6.17 Hz, 1H), 6.85 (br d, J = 5.71 Hz, 1H),
7.13 (m, 2H),7.26 (m, 2H), 7.42 (dt, J = 7.70, 1.51, 1H), 7.65 (d,
J = 7.78 Hz, 1H), 7.73 (d, J = 7.78 Hz, 1H).
(1aR*/S*,7bR*/S*)-1,1-Dichloro-7b-((R*/S*,Z)-8-chloro-6,7-dihy-
dro-7-methoxy-2-methyl-5H-benzo[7]annulen-9-yl)-1a,2,3,7b-
tetrahydro-6-methyl-1H-cyclopropa[a]naphthalene (1c). (Color-
less oil): 1.65 (dd, J = 6.70, 3.73 Hz, 1H), 1.99 (m, 1H), 2.22 (m, 1H),
2.22 (s, 3H), 2.32 (m, 1H), 2.39 (s, 3H), 2.51 (m, 2H), 2.82 (m, 1H),
2.98 (m, 2H), 3.47 (s, 3H), 3.91 (dd, J = 11.99, 5.92 Hz, 1H), 6.61 (s,
1H), 6.98–7.20 (m, 4H), 7.90 (s, 1H).
oil): Endo form. 0.90 (t, J = 6.80 Hz, 3H), 2.16 (m, 1H), 2.22 (s,
3H), 2.38 (m, 1H), 2.40 (s, 3H), 2.52 (m, 1H), 2.64 (m, 2H), 2.74 (m,
1H), 2.88 (m, 2H), 3.28 (m, 2H), 3.36 (m, 1H), 4.32 (dd, J = 5.79,
2.12 Hz, 1H), 6.97–7.21 (m, 5H), 8.11 (s, 1H), exo form. 1.14 (t,
J = 7.01 Hz, 3H), 2.16 (m, 1H), 2.34 (s, 3H), 2.36 (m, 1H), 2.44 (s,
3H), 2.47 (m, 1H), 2.52 (m, 2H), 2.64 (m, 1H), 2.86 (m, 2H), 2.92
(m, 1H), 3.34 (m, 1H), 3.42 (m, 1H), 4.09 (dd, J = 12.12, 6.02 Hz,
1H), 6.64 (br s, 1H), 6.98–7.20 (m, 3H), 7.45 (s, 1H), 7.54 (s, 1H).
Acknowledgments
(1aS*/R*,7bS*/R*)-1,1-Dichloro-7b-((R*/S*,Z)-8-chloro-6,7-dihy-
dro-7-methoxy-2-methyl-5H-benzo[7]annulen-9-yl)-1a,2,3,7b-
tetrahydro-6-methyl-1H-cyclopropa[a]naphthalene (2c). (Color-
less oil): endo form. 2.13 (m, 1H), 2.21 (s, 3H), 2.36 (m, 1H), 2.39 (s,
3H), 2.50 (m, 1H), 2.61 (m, 2H), 2.71 (m, 1H), 2.85 (m, 2H), 3.18 (s,
3H), 3.27 (m, 1H), 4.23 (dd, J = 5.83, 2.11 Hz, 1H), 6.98–7.20 (m,
5H), 8.14 (s, 1H), exo form. 2.13 (m, 1H), 2.32 (s, 3H), 2.36 (m,
1H), 2.43 (s, 3H), 2.46 (m, 1H), 2.50 (m, 2H), 2.61 (m, 1H), 2.85
(m, 2H), 2.88 (m, 1H), 3.19 (s, 3H), 3.99 (dd, J = 12.10, 6.12 Hz,
1H), 6.64 (br s, 1H), 6.98–7.20 (m, 3H), 7.44 (s, 1H), 7.53 (s, 1H).
(1aR*/S*,7bR*/S*)-1,1-Dichloro-7b-((R*/S*,Z)-8-chloro-7-ethoxy-
6,7-dihydro-2-methyl-5H-benzo[7]annulen-9-yl)-1a,2,3,7b-tetra-
hydro-6-methyl-1H-cyclopropa[a]naphthalene (1d). (Colorless
oil): 1.34 (t, J = 6.99 Hz, 3H), 1.66 (dd, J = 6.66, 3.67 Hz, 1H), 2.02
(m, 1H), 2.23 (s, 3H), 2.24 (m, 1H), 2.34 (m, 1H), 2.40 (s, 3H),
2.52 (m, 2H), 2.84 (m, 1H), 3.01 (m, 2H), 3.43 (m, 1H), 3.78 (m,
1H), 4.02 (dd, J = 12.02, 6.21 Hz, 1H), 6.62 (s, 1H), 6.97–7.21 (m,
4H), 7.88 (s, 1H).
Financial support by the research council of University of
Tehran is highly acknowledged.
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