Abstract
The review generalizes the published data on the reactions of vinylic cations generated upon alkyne protonation at the triple bond in proton-donor Br${\oslash}$nsted superacids and Børonsted–Lewis conjugated systems: HSO3F5, CF3SO3H–SbF5, HF–SbF5, HBr–AlBr3 and so on. Characteristics of vinylic cations obtained by physicochemical methods (NMR spectroscopy, X-ray diffraction, IR spectroscopy) are presented. Bibliography — 88 references.
References
1.
1
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR ,
1948
3.
3
M. F. Shostakovskii
"Prostye Vinilovye Efiry" (Vinyl Ethers) ,
1952
4.
Ponomarev D.A., Shevchenko S.M.
Journal of Chemical Education ,
2007
5.
5
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR ,
1953
6.
7.
Olah G.A., Klumpp D.A.
Accounts of Chemical Research ,
2004
8.
Prakash G.K.
Journal of Organic Chemistry ,
2006
9.
Nenajdenko V.G., Shevchenko N.E., Balenkova E.S., Alabugin I.V.
Chemical Reviews ,
2002
10.
Akhrem I., Orlinkov A.
Chemical Reviews ,
2007
11.
Akhrem I.S., Orlinkov A.V., Vol'pin M.E.
Russian Chemical Reviews ,
1996
12.
Rusanov A.L., Chebotarev V.P., Lovkov S.S.
Russian Chemical Reviews ,
2008
13.
Reed C.A.
Chemical Communications ,
2005
14.
Reddy B.M., Patil M.K.
Chemical Reviews ,
2009
15.
15
A. S. Holt
"Research in Photosynthesis" ,
1957
16.
16
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR ,
1949
17.
17
V. B. Evstigneev
Dokl. Akad. Nauk SSSR ,
1958
18.
18
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR ,
1951
19.
Crofton M.W., Jagod M., Rehfuss B.D., Oka T.
Journal of Chemical Physics ,
1989
20.
Winter A.H., Falvey D.E.
Journal of the American Chemical Society ,
2009
21.
22.
Okazaki T., Laali K.K.
Journal of Organic Chemistry ,
2006
23.
23
N. V. Vostrilova
Dokl. Akad. Nauk Uzbek. SSR ,
1958
24.
Koch E., Siehl H., Hanack M.
Tetrahedron Letters ,
1985
25.
Siehl H.U., Kaufmann F.P.
Journal of the American Chemical Society ,
1992
26.
Siehl H.U., Kaufmann F.P., Hori K.
Journal of the American Chemical Society ,
1992
27.
Siehl H., Mueller T., Gauss J., Buzek P., Schleyer P.V.
Journal of the American Chemical Society ,
1994
28.
10.1002/1521-3773(20000901)39:17<3074::AID-ANIE3074>3.0.CO;2-T
29.
Müller T., Juhasz M., Reed C.A.
Angewandte Chemie - International Edition ,
2004
30.
Gauss J., Stanton J.F.
Journal of Molecular Structure THEOCHEM ,
1997
31.
Müller T., Margraf D., Syha Y.
Journal of the American Chemical Society ,
2005
32.
32
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR ,
1952
33.
33
M. B. Neiman
"Issledovanie Mekhanizma Okisleniya Butana" (Research on the Mechanism of the Oxidation of Butane) ,
1939
34.
34
G. W. Robinson
J. Chem. Phys. ,
1886
35.
35
Z. K. Maizus
Dokl. Akad. Nauk SSSR ,
1960
36.
Vasilyev A.V., Walspurger S., Haouas M., Sommer J., Pale P., Rudenko A.P.
Organic and Biomolecular Chemistry ,
2004
37.
Walspurger S., Vasil'ev A.V., Sommer J., Pale P., Savechenkov P.Y., Rudenko A.P.
Russian Journal of Organic Chemistry ,
2005
38.
38
V. B. Evstigneev
Dokl. Akad. Nauk SSSR ,
1956
39.
Aristov S.A., Vasil’ev A.V., Fukin G.K., Rudenko A.P.
Russian Journal of Organic Chemistry ,
2007
40.
Vasilyev A.V., Shchukin A.O., Walspurger S., Sommer J.
European Journal of Organic Chemistry ,
2008
41.
Chassaing S., Specklin S., Weibel J., Pale P.
Tetrahedron ,
2012
42.
42
L. K. Obukhova
Izv. Akad. Nauk SSSR, Otd. Khim. Nauk ,
1960
43.
44.
Stang P.J., Summerville R.
Journal of the American Chemical Society ,
1969
45.
Summerville R.H., Schleyer P.V.
Journal of the American Chemical Society ,
1974
46.
Olah G.A., Spear R.J.
Journal of the American Chemical Society ,
1975
47.
Vasilyev A.V., Walspurger S., Chassaing S., Pale P., Sommer J.
European Journal of Organic Chemistry ,
2007
48.
48
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR ,
1955
49.
50.
10.1002/1521-3773(20021202)41:23<4563::AID-ANIE4563>3.0.CO;2-U
51.
Stereoselective hydrofluorination of ynamides: a straightforward synthesis of novel α-fluoroenamides
Compain G., Jouvin K., Martin-Mingot A., Evano G., Marrot J., Thibaudeau S.
Chemical Communications ,
2012
52.
52
V. B. Evstigneev
Dokl. Akad. Nauk SSSR ,
1957
53.
53
D. Porretand E. Rabinowitch
Nature ,
1937
54.
Khlebnikov A.F., Novikov M.S., Kostikov R.R., Kopf J.
Russian Journal of Organic Chemistry ,
2005
55.
55
G. A. Bogdanovskii
1958
56.
Shchukin A.O., Vasilyev A.V., Rudenko A.P.
Tetrahedron ,
2008
57.
Shchukin A.O., Vasilyev A.V.
Applied Catalysis A: General ,
2008
58.
58
N. E. Khomutov
1953
59.
60.
Zhang Y., Aguirre S.L., Klumpp D.A.
Tetrahedron Letters ,
2002
61.
Klumpp D.A., Rendy, Zhang Y., McElrea A., Gomez A., Dang H.
Journal of Organic Chemistry ,
2004
62.
Rendy, Zhang Y., McElrea A., Gomez A., Klumpp D.A.
Journal of Organic Chemistry ,
2004
63.
Shchukin A.O., Vasil’ev A.V., Grinenko E.V.
Russian Journal of Organic Chemistry ,
2010
64.
Ryabukhin D.S., Vasilyev A.V., Vyazmin S.Y.
Russian Chemical Bulletin ,
2012
65.
65
A. A. Krasnovskii
Biofizika ,
1959
66.
Li H., Jin Y., Wang J., Tian S.
Organic and Biomolecular Chemistry ,
2009
67.
Vasilyev A.V., Walspurger S., Pale P., Sommer J.
Tetrahedron Letters ,
2004
68.
Walspurger S., Vasilyev A.V., Sommer J., Pale P.
Tetrahedron ,
2005
69.
Shklyarenko A.A., Nasledov D.G., Yakovlev V.V.
Russian Journal of Organic Chemistry ,
2005
70.
Koltunov K.Y., Walspurger S., Sommer J.
Chemical Communications ,
2004
71.
Koltunov K., Walspurger S., Sommer J.
European Journal of Organic Chemistry ,
2004
72.
Ryabukhin D.S., Vasil’ev A.V.
Russian Journal of Organic Chemistry ,
2008
73.
Ryabukhin D.S., Fukin G.K., Cherkasov A.V., Vasil’eva A.V.
Russian Journal of Organic Chemistry ,
2009
74.
Ryabukhin D.S., Vasil’ev A.V., Grinenko E.V.
Russian Journal of Organic Chemistry ,
2011
75.
Otani T., Kunimatsu S., Takahashi T., Nihei H., Saito T.
Tetrahedron Letters ,
2009
76.
Kitamura T., Takachi T., Kawasato H., Taniguchi H.
Journal of the Chemical Society Perkin Transactions 1 ,
1992
77.
Zhang Y., Hsung R.P., Zhang X., Huang J., Slafer B.W., Davis A.
Organic Letters ,
2005
78.
Zhang L., Kozmin S.A.
Journal of the American Chemical Society ,
2004
79.
Zhang L., Sun J., Kozmin S.A.
Tetrahedron ,
2006
80.
Jin T., Uchiyama J., Himuro M., Yamamoto Y.
Tetrahedron Letters ,
2011
81.
Jin T., Himuro M., Yamamoto Y.
Journal of the American Chemical Society ,
2010
82.
Sun J., Kozmin S.A.
Journal of the American Chemical Society ,
2005
83.
Yoshida M., Fujino Y., Doi T.
Organic Letters ,
2011
84.
Kitamura T., Takachi T., Miyaji M., Kawasato H., Taniguchi H.
Journal of the Chemical Society Perkin Transactions 1 ,
1994
85.
Matsnev A., Noritake S., Nomura Y., Tokunaga E., Nakamura S., Shibata N.
Angewandte Chemie - International Edition ,
2009
86.
Corma A., García H.
Chemical Reviews ,
2002
87.
Corma A., García H.
Chemical Reviews ,
2003
88.
Sartori G., Maggi R.
Chemical Reviews ,
2006
89.
Busca G.
Chemical Reviews ,
2007