Reactions of the stable 1-benzoselenopyrylium salts 1 with several nucleophiles (methoxide ion, isopropoxide ion, tert-butoxide ion, diethylamine and n-butylamine) and also LiAlH4 reduction are described; comparison of the behaviour of 1-benzotelluropyrylium salts is made.
References
1.
This paper constitutes Part 16 in the series “Studies on Tellurium-Containing Heterocycles”, Part 15, SashidaH., and MinamidaH., J. Chem. Res(s), 2000, 569–571.
2.
DoddiG., and ErcolaniG., Advances in Heterocyclic Chemistry: Thiopyrylium, Selenopyrylium and Telluropyrylium Salts, vol. 60. ed. KatritzkyA.R., Academic Press, Inc., London, 1994, pp. 65–195.
3.
BalabanA.T., DinculescuA., DorofeenkoG. N., FischerG. W., KoblikA. V., MezheritskiiV. V., and SchrothW., Advances in Heterocyclic Chemistry, Supplement 2: Pyrylium Salts: Synthesis, Reactions and Physical Properties, ed. KatritzkyA.R., Academic Press, Inc., London, 1982, pp. 66–73.
4.
KuthanJ., S˘ebekP., and BöhmS., Advances in Heterocyclic Chemistry: Develpoments in the Chemistry of Thiopyrans, Selenopyrans and Telluropyrans, vol. 59, Academic Press, 1994, pp. 179–244.
5.
(a) SadekovI.D., and MinkinV. I., Advances in Heterocyclic Chemistry: Six-Membered Heterocycles with a Tellurium Atom. vol. 63. ed. KatritzkyA.R., Academic Press, Inc., London, 1995, pp. 1–60
6.
DettyM.R., and O'ReganM. R., The Chemistry of Heterocyclic Compounds, vol. 53, ed. TaylorE.C., John Wiley & Sons, Inc., New York, 1994, pp. 219–291.
7.
(a) SashidaH., KurahashiH., and TsuchiyaT., J. Chem. Soc., Chem. Commun., 1991, 802.
8.
SashidaH., ItoK., and TsuchiyaT., J. Chem. Soc., Chem. Commun., 1993, 1493.
9.
SashidaH., ItoK., and TsuchiyaT., Chem. Pharm. Bull., 1995, 43, 19
10.
SashidaH., SadamoriK., and TsuchiyaT., Synth. Commun., 1998, 28, 713
11.
SashidaH., and KawamukaiA., J. Heterocycl. Chem., 1998, 35, 165
12.
SashidaH., and YasuikeS., J. Heterocycl. Chem., 1998, 35, 725
13.
SashidaH., KurodaA., and TsuchiyaT., Chem. Commun., 1998, 767.
14.
SashidaH., Heterocycles, 1998, 48, 631
15.
SashidaH., Synthesis, 1999, 1866.
16.
SashidaH., Heterocycles, 2000, 53, 49.
17.
SashidaH., Synthesis, 1998, 745.
18.
SashidaH., and OhyanagiK., J. Chem. Soc., Perkin Trans. 1, 1998, 2123.
19.
SashidaH., and OhyanagiK., Heterocycles, 1999, 51, 17.
20.
SashidaH., and MinamidaH., J. Chem. Soc., Perkin Trans. 1, 1999, 1665.
HoriM., KataokaT., ShimizuH., TsutsumiK., and ImaokaS., Heterocycles, 1987, 26, 2365.
23.
Semiempirical MO calculations were carried out with Hyper Chem 5.1 software (Hypercube Inc., Gainesville, USA). The PM3 program is parameterized by fitting to experimentally determined Hf for a number of molecules at 298 K.
24.
(a) DoddiG., IlluminatiG., InsamN., and StegelF., J. Org. Chem., 1982, 47, 960
25.
DoddiG., and ErcolaniG., J. Chem. Soc., Perkin Trans. II, 1986, 271.
26.
DoddiG., and ErcolaniG., J. Org. Chem., 1986, 51, 4385
27.
DoddiG., ErcolaniG., and MencarelliP., J. Org. Chem., 1992, 57, 4431.
