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Mendeleev Commun., 2009, 19, 49–51
11 A. V. Borisov, Yu. A. Nikonova, G. N. Borisova, V. K. Osmanov, Zh. V.
Matsulevich and G. V. Zatonskii, Khim. Geterotsikl. Soedin., 2002, 855
[Chem. Heterocycl. Compd. (Engl. Transl.), 2002, 38, 759].
12 A. V. Borisov, T. V. Goncharova, V. K. Osmanov, G. N. Borisova, Zh. V.
Matsulevich, N. G. Frolova and E. D. Savin, Khim. Geterotsikl. Soedin.,
2002, 1305 [Chem. Heterocycl. Compd. (Engl. Transl.), 2002, 38,
1146].
13 A. V. Borisov, G. N. Borisova, Yu. A. Nikonova, V. K. Osmanov and
Zh. V. Matsulevich, Khim. Geterotsikl. Soedin., 2003, 1273 [Chem.
Heterocycl. Compd. (Engl. Transl.), 2003, 39, 1261].
mechanism of the reaction is supported by experimental observa-
tions. Thus, reactions of hetarene sulfenyl chlorides with cyclic
and bicyclic alkenes lead exclusively to the formation of the
cis-fused products.12,16,17 The formation of skeletal-rearrange-
ment products of heterocyclization in the sulfenylation of
3,3-dimethyl-1-butene15 and 3,4,5,6-tetrafluorotricyclo[6.2.2.02,7]-
dodeca-2(7),3,5,9,11-pentaene14 suggests also the carbocationic
reaction mechanism.
14 A. V. Borisov, G. N. Borisova, Yu. A. Nikonova, V. K. Osmanov and
Zh. V. Matsulevich, Khim. Geterotsikl. Soedin., 2003, 1431 [Chem.
Heterocycl. Compd. (Engl. Transl.), 2003, 39, 1119].
15 A. V. Borisov, V. K. Belsky, T. V. Goncharova, G. N. Borisova, V. K.
Osmanov, Zh. V. Matsulevich, N. G. Frolova and E. D. Savin, Khim.
Geterotsikl. Soedin., 2005, 893 [Chem. Heterocycl. Compd. (Engl.
Transl.), 2005, 41, 771].
16 A. V. Borisov, V. K. Osmanov, Yu. A. Nikonova, G. N. Borisova and
Zh. V. Matsulevich, Khim. Geterotsikl. Soedin., 2005, 925 [Chem.
Heterocycl. Compd. (Engl. Transl.), 2005, 41, 806].
17 A. V. Borisov, V. K. Osmanov, I. G. Sokolov, G. N. Borisova and
Zh. V. Matsulevich, Khim. Geterotsikl. Soedin., 2006, 303 [Chem.
Heterocycl. Compd. (Engl. Transl.), 2006, 42, 272].
18 G. Le Fevre, S. Sinbandhit and J. Hamelin, Tetrahedron, 1979, 35,
1821.
19 Q. Wang, A. Amer, S. Mohr, E. Ertel and J. C. Jochims, Tetrahedron,
1993, 49, 9973.
20 S. Ohsugi, K. Nishide and M. Node, Tetrahedron, 2003, 59, 1859.
21 G. M. Sheldrick, SHELXTL, v. 6.12, Structure Determination Software
Suite, Bruker AXS, Madison, Wisconsin, USA, 2000.
22 G. M. Sheldrick, SADABS v.2.01, Bruker/Siemens Area Detector Absorp-
tion Correction Program, Bruker AXS, Madison, Wisconsin, USA,
1998.
This work was supported by the Foundation of the President
of the Russian Federation (Federal Programme for the Support of
Leading Scientific Schools, grant no. NSh 1396.2008.3) and the
Russian Foundation for Basic Research (project no. 06-03-32728-a).
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Received: 19th June 2008; Com. 08/3156
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