20.1 縮合多環芳香族化合物の反 応

20.1

CCl₄ Br₂

H.T Clarke, M,R. Brethen,

Org. Synth., Coll. Vol. 1, 121 (1941).

72~75%

Br

/

reflux, 12~15 h

OH

2 AcOH

OH Br

Br

OH Br

HBr, Sn

C.F. Koelsch, Org. Synth., Coll. Vol. 3, 132 (1955).

96~100%

NHAc

AcOH HNO3

NHAc NO

W.W. Hartman, L.A. Smith,

Org. Synth., Coll. Vol. 2, 438 (1943).

40 ˚C

47~48%

OH

NaNO₂ H₂SO₄

OH NO

C.S. Marvel, P.K. Porter,

Org. Synth., Coll. Vol. 1, 411 (1941).

0 ˚C

99%

OH NO

OH NH

SO

H

1) NaHSO₃, NaOH, H₂O

2) H₂SO₄

L.F. Fieser,

Org. Synth., Coll. Vol. 2, 42 (1943).

83%

O O

O

AlCl₃

O CO

H

+

nitrobenzene 0 ˚C, 5 h

L.F. Fieser,

Org. Synth., Coll. Vol. 3, 6 (1955).

81%

CO

H

MeSO₃H

O

90~95 ˚C

65%

V. Premasagar, V.A. Palaniswamy, E.J. Eisenbraun, J. Org. Chem., 46, 2974 (1981).

AlCl₃ CH₃COCl

MeO MeO

COCH

OMe

COCH

nitrobenzene

10.5~13 ˚C

45~48%

+

!"#

OMe

AlCl₃

CH₃COCl

OMe

COCH

CS₂, < 0 ˚C

  L. Arsenijevic, et al., Org. Synth., Coll. Vol. 6, 34 (1988).

OEt OEt

CHO

+ HCONHPh

2) H2O

74~84%

J.H. Wood, R.W. Bost, Org. Synth., Coll. Vol. 3, 98 (1955).

Vilsmeier !"

OH

EtOH

!

OH CHO

CHCl₃, NaOH

Reimer-Tiemann !"

A. Russell, L.B. Lockhart,

Org. Synth., Coll. Vol. 3, 463 (1955).

38~48%

CH

Cl

CH₂O, HCl H₃PO₄, AcOH

80~85 ˚C

O. Grummitt, A. Buck,

Org. Synth., Coll. Vol. 3, 195 (1955).

74~77%

Br₂ CCl₄

Br

Br

I.M. Heilbron, J.S. Heaton,

Org. Synth., Coll. Vol. 1, 207 (1941).

83~88%

CuCl₂ CCl₄

Cl

D.C. Nonhebel,

Org. Synth., Coll. Vol. 5, 206(1973).

75~80%

reflux, 20 h

HCl AcOH HNO₃

NO

Cl

H₂O NaOH

NO

C.E. Braun, et al., Org. Synth., Coll. Vol. 4, 711 (1963).

60~68%

AlCl₃ CH₃COCl

O CH

benzene 0 ˚C

C. Merritt, Jr., C.E. Braun, Org. Synth., Coll. Vol. 4, 8 (1963).

57~60%

HC N Ph Me O

POCl₃

CHO

L.F. Fieser, et al.,

Org. Synth., Coll. Vol. 3, 98 (1955).

Vilsmeier !"

77~84%

o-dichlorobenzene 90~95 ˚C

CCl₄ Br₂

!

Br

C.A. Dornfeld, J.E. Callen, G.H. Coleman, Org. Synth., Coll. Vol. 3, 134 (1955).

90~94%

H₂SO₄

SO

H (SO

H)

L.F. Fieser, Org. Synth., Coll. Vol. 2, 482 (1943).

120 ˚C, 3.5 h

Barium 2-phenanthrenesulfonate: 17~21% yield Potassium 3-phenanthrenesulfonate: 24~26% yield

Br₂ CCl₄

Br

W.H. Gumprecht,

Org. Synth., Coll. Vol. 5, 147!(1973).

78~86%