OSR 18.2
芳香族求核置換反応
目次： 付加−脱離機構
脱離−付加機構
ジアゾニウム塩の置換反応
（ジアゾカップリングについては OSR 16 を見ること）
NH2 → OH
NH2 → ハロゲン
NH2 → CN, NO2, N3
NH2 → その他の官能基
NH2 → H
付加−脱離機構
F.B. Welles, C.F.H. Allen, Org. Synth., Coll. Vol. 2, 221 (1943).
C.F.H. Allen, Org. Synth., Coll. Vol. 2, 228 (1943).
H.P. Schultz, Org. Synth., Coll. Vol. 4, 364 (1963).
J.H. Boyer, R.S. Burks, Org. Synth., Coll. Vol. 5, 1067 (1973).
1
N. Kharasch, R.B. Langford, Org. Synth., Coll. Vol. 5, 474 (1973).
C.C. Price, G.W. Stacy, Org. Synth., Coll. Vol. 3, 86 (1955).
See also M.T. Bogert, A. Stull, Org. Synth., Coll. Vol. 1, 220 (1941).
R. Filler, S.M. Woods, Org. Synth., Coll. Vol. 6, 873 (1988).
M.E. Dudley, M.M. Morshed, M.M. Hossain, Org. Synth., 86, 172 (2009).
（脱離−付加機構ならメタ体が優先される）
S. Caron, J. M. Wojcik, and E. Vazquez, Org. Synth., Coll. Vol. 10, 505 (2004).
2
脱離−付加機構
R.V. Sahyun, D.J. Cram, Org. Synth., Coll. Vol. 5, 926 (1973).
ジアゾニウム塩の置換反応
NH2 → OH
R.H.F. Manske, Org. Synth., Coll. Vol. 1, 404 (1941).
R.B. Woodward, Org. Synth., Coll. Vol. 3, 453 (1955).
H.E. Ungnade, E.F. Orwoll, Org. Synth., Coll. Vol. 3, 130 (1955).
K. Dimroth, A. Berndt, H. Perst, C. Reichardt, Org. Synth., Coll. Vol. 5, 1130 (1973).
NH2 → ハロゲン
（パラ体も同じように合成できる）
C.S. Marvel, S.M. McElvain, Org. Synth., Coll. Vol. 1, 170 (1941).
3
W.W. Hartman, M.R. Brethen, Org. Synth., Coll. Vol. 1, 162 (1941).
F.D. Gunstone, S.H. Tucker, Org. Synth., Coll. Vol, 4, 160 (1963).
J.S. Buck, W.S. Ide, Org. Synth., Coll. Vol. 2, 130 (1943).
L.A. Bigelow, Org. Synth., Coll. Vol. 1, 135 (1941).
L.A. Bigelow, Org. Synth., Coll. Vol. 1, 136 (1941).
J.L. Hartwell, Org. Synth. Coll., Vol. 3, 185 (1955).
H.J. Lucas, E.R. Kennedy, Org. Synth., Coll. Vol. 2, 351 (1943).
4
F.B. Dains, F. Eberly, Org. Synth., Coll. Vol. 2, 355 (1943).
R.B. Sandin, T.L. Cairns, Org. Synth., Coll. Vol. 2, 604 (1943).
D.T. Flood, Org. Synth., Coll. Vol. 2, 295 (1943).
G. Schiemann, W. Winkelmüler, Org. Synth., Coll. Vol. 2, 299 (1943).
G. Schiemann, W. Winkelmüler, Org. Synth., Coll. Vol. 2, 188 (1943).
K.G. Rutherford, W. Redmond, Org. Synth., Coll. Vol. 5, 133 (1973).
NH2 → CN, NO2, N3
（パラ体も同じように合成できる）
H.T. Clarke, R.R. Read, Org. Synth., Coll. Vol. 1, 514 (1941).
5
E.B. Starkey, Org. Synth., Coll. Vol. 2, 225 (1943).
H.H. Hodgson, A.P. Mahadevan, E.R. Ward, Org. Synth., Coll. Vol. 3, 341 (1955).
G.D. Mendenhall, P.A.S. Smith, Org. Synth., Coll. Vol. 5, 829 (1973).
NH2 → その他の官能基
C.F.H. Allen, D.D. MacKay, Org. Synth., Coll. Vol. 2, 580 (1943).
D.S. Tarbell, D.K. Fukushima, Org. Synth., Coll. Vol. 3, 809 (1955).
R.V. Hoffman, Org. Synth., Coll. Vol. 7, 508 (1990).
6
G.A, Ropp, E.C. Coyner, Org. Synth., Coll. Vol. 4, 727 (1963).
NH2 → H
N. Kornblum, Org. Synth., Coll. Vol. 3, 295 (1955).
7

OSR 19.1 多環芳香族化合物の反応

Senior Roster LC 2013 SWAT- Mil JR/SR Gold Jr/Sr. Gold

OSR 13 脱離