SRN1 Reaction of Haloarenes with Benzenethiolate, Benzeneselenolate, and Benzenetellurolate Ions 541
1500, 1420, 1380, 1310, 1120, 1030, 960, 800, 690;
7.26–8.50 (m, ArH).
Eds.; Wiley: Chichester, U.K., 1983; Supplement D,
Chapter 16; (b) Rossi, R. A.; de Rossi, R. H. Aromatic
Substitution by the SRN1 Mechanism; ACS Mono-
graph 178; American Chemical Society: Washington,
DC, 1983; (c) Norris, R. K. Comprohensive Organic
Synthesis; Trost, B. M., Ed.; Pergamon press, Elms-
furd, NY, 1991; Vol. 4, p 451.
H
1
5: 5-Phenylselenoquinoline oil [12]; max/cm
3030, 1620, 1590, 1570, 1500, 1420, 1380, 1310, 1120,
1030, 960, 800, 760, 690; 7.20–8.35 (m, ArH).
H
6: 2-Phenyltelluroquinoline, m.p. 42–45 C (lit.
1
[2] (a) Kim, J. K.; Bunnett, J. F. J Am Chem Soc 1970,
92, 7463; (b) Scamehorm, R. G.; Bunett, J. F. J
Org Chem 1977, 42, 1449; (c) Scamehorm, R. G.;
Hardacre, J. M.; Lukanich, J. M. J Org Chem 1984, 49,
4881.
[3] Fox, M. A.; Younathan, J.; Fryxell, G. E. J Org Chem
1983, 48, 3109.
[4] Rossi, R. A.; Bunnett, J. F. J Am Chem Soc 1974, 96,
112.
[5] (a) Saveant, J. M. Acc Chem Res 1980, 13, 323; (b)
Saveant, J. M. Adv Phys Org Chem 1990, 26, 1 and
references cited therein.
[6] (a) Galli, C.; Gentile, P. J Chem Soc Perkin Trans 2,
1993, 1135; (b) Leeuwen, M. V.; Mckillop, A. J Chem
Soc Perkin Trans 1, 1993, 2433.
[7] Nazareno, M. A.; Rossi, R. A. Tetrahedron Lett.; 1994,
35, 5185.
[8] Curran, D. P.; Fevig, T. L.; Jaspers, C. P.; Totleeben,
M. J. Synlett 1992, 943 and references cited therein.
[9] Syper, L.; Mlochowski, J. Synthesis 1984, 5, 439.
[10] Engman, L.; Persson, J. Synth Commun 1993, 23,
445.
[11] Fukuzawa, S.; Niimoto, Y.; Fujinami, T.; Sakai, S.
Heteroat Chem 1991, 1, 490.
[12] 46–48 C); max/cm 3030, 3010, 2980, 1620,
1590, 1570, 1500, 1410, 1380, 1310, 1030, 960, 810,
760, 690;
7.30–8.40(m, ArH).
7: 1-Phenylthionaphthalene oil [13]; max/cm
3030, 1580, 1500, 1480, 1440, 1380, 1020, 970, 800,
770, 740, 690; 7.70–8.90 (m, ArH).
H
1
H
8: 1-Phenylselenonaphthalene, m.p. 50 C (lit. [14]
1
52–53 C); max/cm 3030, 1580, 1500, 1480, 1440,
1380, 1010, 970, 770, 710, 690; H ∧ 7.00–8.30
(m, ArH).
1
9: Phenyltelluronaphthalene, oil [15]; max/cm
3030, 1600, 1480, 1440, 1380, 1010, 970, 770, 710,
690;
7.00–8.35 (m, ArH).
H
10: 1-Phenylthioadamantane, m.p. 68–71 C (lit.
1
[16] 71.5-72 C); max/cm 3060, 3040, 2950, 1590,
1580, 1500, 1450, 1380, 1350, 1270, 1220, 960, 690;
1.65–2.40 (m, 15H), 7.08–7.85 (m, 5H).
H
11: 1-Phenylselenoadamantane, low melting crys-
1
tal m.p.(lit. [17] 35 C); max/cm 3040, 2940, 1600,
1580, 1500, 1450, 1380, 1340, 1270, 950, 690;
H
[12] Pierini, A. B.; Penenory, A. B.; Rossi, R. A. J Org
Chem 1984, 49, 486.
[13] Cristau, H. J.; Chabaud, B.; Labaudiniere, R.;
Christol, H. Organometallics 1985, 4, 657.
[14] Baumgartner, M. T.; Pierini, A. B.; Rossi, R. A. J Org
Chem 1993, 58, 2593.
1.60–2.22 (m, 15H), 7.10–7.95 (m, 5H).
12: 1-Phenyltelluroadamantane, m.p. 110–112 C
1
(lit. [17] 113–115 C); max/cm 3040, 2945, 1590,
1500, 1450, 1380, 1340, 1280, 960, 690; H ∧ 1.65–2.25
(m, 15H), 7.06–7.75 (m, 5H).
[15] Fujihara, H.; Ishitani, H.; Takaguchi, Y.; Furukawa,
N. Chem Lett 1995, 171, 571.
[16] Hoffman, R. W.; Julius, M.; Chemla, F.; Ruhland, T.;
Frenzen, G. Tetrahedron 1994, 50, 6049.
[17] Okada, K.; Okubo, K.; Morita, N.; Oda, M. Chem Lett
1993, 2021.
REFERENCES
[1] For reviews, see: (a) Norris, R. K. The Chem-
istry of Functional Groups; Patai, S., Rappoport, Z.,