M. Nazari, B. Movassagh / Tetrahedron Letters 50 (2009) 438–441
441
the corresponding arylselenenyl-functionalized carboxylic acid. All new
compounds have been characterized by 1H and 13C NMR, IR, mass
spectroscopy, and elemental analysis. Compound 4g: mp 100–101 °C. IR
References and notes
1. (a) Back, T. G. Organoselenium Chemistry:
A Practical Approach; Oxford
(KBr)
m ; d 1.99 (quin,
1709, 2450–3500 cmÀ1 1H NMR (300 MHz, CDCl3)
University Press: Oxford, UK, 1999; (b) Liotta, D. Organoselenium Chemistry;
Wiley: New York, 1987.
J = 7.2 Hz, 2H), 2.51 (t, J = 7.2 Hz, 2H), 2.94 (t, J = 7.3 Hz, 2H), 7.24 (d, J = 8.5 Hz,
2H), 7.43 (d, J = 8.5 Hz, 2H), 11.50 (br s, 1H); 13C NMR (75 MHz, CDCl3) d 24.8,
27.1, 33.5, 127.7, 129.3, 133.3, 134.2, 179.3; MS (EI): m/z (%) = 280 (10) [M+4]+,
278 (24) [M+2]+, 276 (11) [M]+, 192 (21), 156 (16), 112 (24), 87 (100), 43 (44).
Anal. Calcd for C10H11ClO2Se: C, 43.27; H, 3.99. Found: C, 43.16; H, 3.83.
2. (a) Mugesh, G.; du Mont, W. W.; Sies, H. Chem. Rev. 2001, 101, 2125; (b)
Malmstrom, J.; Jonsson, M.; Cotgreave, I. A.; Hammarstrom, L.; Sjodin, M.;
Engman, L. J. Am. Chem. Soc. 2001, 123, 3434; (c) Back, T. G.; Moussa, Z. J. Am.
Chem. Soc. 2003, 125, 13455; (d) Lucas, M. A.; Nagugen, O. T. K.; Schiesser, C. H.;
Zheng, S. L. Tetrahedron 2000, 56, 3995.
3. (a) Sharpless, K. B.; Lauer, R. F. J. Am. Chem. Soc. 1973, 95, 2697; (b) Sharpless, K.
B.; Lauer, R. F.; Teranishi, A. Y. J. Am. Chem. Soc. 1973, 95, 6137; (c) Grieco, P. A.;
Gilman, S.; Nishizawa, M. J. Org. Chem. 1976, 41, 1485; (d) Zhang, Y.; Yu, Y.; Lin,
R. Synth. Commun. 1993, 23, 189; (e) Suzuki, H.; Yoshinaga, M.; Takaoka, K.;
Hiroi, Y. Synthesis 1985, 497.
Compound 4h: IR (neat)
m ;
1714 cmÀ1 1H NMR (500 MHz, CDCl3) d 1.96 (quin,
J = 7.1 Hz, 2H), 2.13 (s, 3H), 2.59 (t, J = 7.0 Hz, 2H), 2.91 (t, J = 7.2 Hz, 2H), 7.24
(d, J = 8.5 Hz, 2H), 7.43 (d, J = 8.5 Hz, 2H); 13C NMR (125 MHz, CDCl3) d 23.9,
27.5, 30.0, 42.9, 128.2, 129.2, 133.1, 134.0, 207.7; MS (EI): m/z (%) 278 (7)
[M+4]+, 276 (15) [M+2]+, 274 (7) [M]+, 191 (4), 156 (3), 125 (3), 85 (100), 43
(86). Anal. Calcd for C11H13ClOSe: C, 47.93; H, 4.75. Found: C, 47.83; H, 4.39.
Compound 4i: IR (neat)
m ;
1708, 2400–3500 cmÀ1 1H NMR (500 MHz, CDCl3) d
4. (a) Scarborough, R. M., Jr.; Toder, B. H.; Smith, A. B., III. J. Am. Chem. Soc. 1980,
102, 3904; (b) Smith, A. B.; Scarborough, R. M., Jr. Tetrahedron Lett. 1978, 1649;
(c) Meinwald, J.; Crandall, K. J. Am. Chem. Soc. 1966, 88, 1292.
2.01 (quin, J = 7.2 Hz, 2H), 2.53 (t, J = 7.3 Hz, 2H), 3.02 (t, J = 7.2 Hz, 2H), 7.41 (t,
J = 7.7 Hz, 1H), 7.51–7.63 (m, 2H), 7.80–7.90 (m, 3H), 8.45 (d, J = 8.4 Hz, 1H),
11.41 (br s, 1H); 13C NMR (125 MHz, CDCl3) d 25.0, 27.1, 33.8, 125.8, 126.3,
126.7, 127.6, 128.5, 128.7, 129.1, 132.5, 134.1, 134.4, 179.3; MS (EI): m/z (%)
294 (87) [M + 2]+, 292 (47) [M]+, 208 (38), 141 (14), 128 (100), 115 (65), 87
(67), 43 (24). Anal. Calcd for C14H14O2Se: C, 57.35; H, 4.81. Found: C, 56.99; H,
5.03.
5. (a) Liotta, D.; Sunay, U.; Santiesteban, H.; Markiewicz, W. J. Org. Chem. 1981, 46,
2605; (b) Liotta, D.; Markiewicz, W.; Santiesteban, H. Tetrahedron Lett. 1977,
4365; (c) Liotta, D.; Santiesteban, H. Tetrahedron Lett. 1977, 4369; (d)
Scarborough, R. M., Jr.; Smith, A. B. Tetrahedron Lett. 1977, 4361.
6. (a) Movassagh, B.; Tatar, A. Synlett 2007, 1954; (b) Movassagh, B.; Mirshojaei, F.
Monatsh. Chem. 2003, 134, 831; (c) Movassagh, B.; Shamsipoor, M. Synlett 2005,
1316; (d) Movassagh, B.; Fazeli, A. Z. Naturforsch. 2006, 61B, 194; (e)
Movassagh, B.; Shamsipoor, M.; Joshaghani, M. J. Chem. Res. (S) 2004, 148; (f)
Movassagh, B.; Shamsipoor, M. Synlett 2005, 127; (g) Movassagh, B.; Fazeli, A.
Monatsh. Chem. 2007, 138, 863.
Compound 4j: IR (neat)
m ;
1714 cmÀ1 1H NMR (500 MHz, CDCl3) d 1.96 (quin,
J = 7.1 Hz, 2H), 2.13 (s, 3H), 2.59 (t, J = 7.1 Hz, 2H), 2.99 (t, J = 7.1 Hz, 2H), 7.40 (t,
J = 7.7 Hz, 1H), 7.50–7.62 (m, 2H), 7.78–7.89 (m, 3H), 8.40 (d, J = 8.4 Hz, 1H);
13C NMR (125 MHz, CDCl3) d 24.0, 27.5, 29.7, 43.1, 125.8, 126.2, 126.6, 127.5,
128.3, 128.7, 129.2, 132.3, 134.1, 134.3, 207.9; MS (EI): m/z (%) 292 (17) [M+2]+,
290 (10) [M]+, 207 (6), 165 (6), 141 (6), 128 (15), 115 (17), 85 (100), 43 (99).
Anal. Calcd for C15H16OSe: C, 61.86; H, 5.54. Found: C, 62.17; H, 5.76.
8. Monahan, R.; Brown, D.; Waykole, L.; Liotta, D. In Organoselenium Chemistry;
Liotta, D., Ed.; Wiley: New York, 1987.
9. (a) McMurry, J. Org. React. 1977, 24, 187; (b) Bartlett, P. A.; Johnson, W. S.
Tetrahedron Lett. 1970, 4459; (c) Müller, P.; Siegfried, B. Helv. Chim. Acta 1974,
57, 987.
10. In the absence of AlCl3 no nucleophilic cleavage of lactones or esters was
observed.
7. General procedure:
A mixture of diaryl diselenide (0.5 mmol), zinc dust
(3.0 mmol), and dry MeCN (15 mL) was stirred at 70 °C. After 15 min,
anhydrous AlCl3 (2.5 mmol) in dry MeCN (2 mL) was added to the reaction
mixture cautiously. The mixture was stirred for about 1 h at 70 °C until the
yellow solution became colorless. Then, lactone or ester (1.05 mmol) was
added to the solution, and the mixture was stirred at 70 °C for the time
specified in Tables 1 and 2. The progress of the reaction was monitored by TLC.
After the reaction was complete, the solution was filtered and the solvent was
evaporated. Aqueous 10% HCl (30 mL) was added to the crude product which
was extracted with EtOAc (3 Â 30 mL). The organic layer was dried over
anhydrous Na2SO4 and the solvent was removed under reduced pressure.
Purification by preparative TLC (silica gel, eluent, n-hexane–EtOAc = 2:1) gave
11. (a) The isolated yield was 32% after 50 h; (b) The isolated yield was 30% after
52 h.
12. Merck Catalogue, 2005–2007.