Abstract
This review deals with the methods of supramolecular chemistry used for controlling the efficiency and stereoselectivity of intermolecular [2+2] photocycloaddition of olefins and other unsaturated compounds in homogeneous solutions. The best-studied methods are self-assembly through cation--macrocycle interactions, complexation with molecular templates through hydrogen bonding, and confinement of the reactants in supramolecular containers. The possibilities of using anionic templates and combined supramolecular approaches are discussed.
The bibliography includes 107~references.
References
2.
Hoffmann N.
Chemical Reviews ,
2008
3.
Bach T., Hehn J.P.
Angewandte Chemie - International Edition ,
2011
4.
5.
5
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR ,
1953
6.
Hirayama F., Utsuki T., Uekama K.
Journal of the Chemical Society Chemical Communications ,
1991
7.
Alfimov M.V., Gromov S.P., Stanislavskii O.B., Ushakov E.N., Fedorova O.A.
Russian Chemical Bulletin ,
1993
8.
8
V. N. Kondrat'ev
"Kinetika Reaktsii v Gazovoi Faze" (Kinetics of Reactions in the Gas Phase) ,
1959
9.
Beak P., Zeigler J.M.
Journal of Organic Chemistry ,
1981
10.
Bach T., Bergmann H.
Journal of the American Chemical Society ,
2000
11.
Svoboda J., König B.
Chemical Reviews ,
2006
12.
Bibal B., Mongin C., Bassani D.M.
Chemical Society Reviews ,
2014
13.
Barzykin A.V., Fox M.A., Ushakov E.N., Stanislavskii O.B., Gromov S.P., Fedorova O.A., Al'fimov M.V.
Journal of the American Chemical Society ,
1992
14.
Ushakov E.N., Gromov S.P., Buevich A.V., Baskin I.I., Fedorova O.A., Vedernikov A.I., Alfimov M.V., Eliasson B., Edlund U.
Journal of the Chemical Society Perkin Transactions 2 ,
1999
15.
10.1002/1522-2675(200201)85:1<60::AID-HLCA60>3.0.CO;2-C
16.
Amirsakis D.G., Elizarov A.M., Garcia-Garibay M.A., Glink P.T., Stoddart J.F., White A.J., Williams D.J.
Angewandte Chemie - International Edition ,
2003
17.
Gromov S.P., Lobova N.A., Vedernikov A.I., Kuz’mina L.G., Howard J.A., Alfimov M.V.
Russian Chemical Bulletin ,
2009
18.
18
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR ,
1951
19.
Gromov S.P., Vedernikov A.I., Lobova N.A., Kuz’mina L.G., Dmitrieva S.N., Strelenko Y.A., Howard J.A.
Journal of Organic Chemistry ,
2014
20.
Gromov S.P.
Russian Chemical Bulletin ,
2008
21.
21
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR ,
1958
22.
Ushakov E.N., Alfimov M.V., Gromov S.P.
Russian Chemical Reviews ,
2008
23.
Ushakov E.N., Alfimov M.V., Gromov S.P.
Macroheterocycles ,
2010
24.
Gromov S.P., Fedorova O.A., Ushakov E.N., Buevich A.V., Alfimov M.V.
Russian Chemical Bulletin ,
1995
25.
25
G. W. Robinson
J. Chem. Phys. ,
1955
26.
Gromov S.P., Ushakov E.N., Fedorova O.A., Buevich A.V., Alfimov M.V.
Russian Chemical Bulletin ,
1996
27.
27
A. A. Krasnovskii
Biofizika ,
1956
28.
Gromov S.P., Fedorova O.A., Ushakov E.N., Baskin I.I., Lindeman A.V., Malysheva E.V., Balashova T.A., Arsen'ev A.S., Alfimov M.V.
Russian Chemical Bulletin ,
1998
29.
29
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR ,
1951
30.
Fedorova O.A., Fedorov Y.V., Vedernikov A.I., Gromov S.P., Yescheulova O.V., Alfimov M.V., Woerner M., Bossmann S., Braun A., Saltiel J.
Journal of Physical Chemistry A ,
2002
31.
Gromov S.P., Ushakov E.N., Fedorova O.A., Baskin I.I., Buevich A.V., Andryukhina E.N., Alfimov M.V., Johnels D., Edlund U.G., Whitesell J.K., Fox M.A.
Journal of Organic Chemistry ,
2003
32.
Ushakov E.N., Vedernikov A.I., Alfimov M.V., Gromov S.P.
Photochemical and Photobiological Sciences ,
2011
33.
Pedersen C.J.
Journal of the American Chemical Society ,
1970
34.
Gromov S.P., Fedorova O.A., Ushakov E.N., Buevich A.V., Baskin I.I., Pershina Y.V., Eliasson B., Edlund U., Alfimov M.V.
Journal of the Chemical Society Perkin Transactions 2 ,
1999
35.
Gromov S.P., Vedernikov A.I., Fedorov Y.V., Fedorova O.A., Andryukhina E.N., Shepel' N.E., Strelenko Y.A., Johnels D., Edlund U., Saltiel J., Alfimov M.V.
Russian Chemical Bulletin ,
2005
36.
36
J. Billon
Bull. Soc. chim. France ,
1960
37.
Gromov S.P., Vedernikov A.I., Lobova N.A., Kuz'mina L.G., Basok S.S., Strelenko Y.A., Alfimov M.V., Howard J.A.
New Journal of Chemistry ,
2011
38.
Fedorov Y.V., Fedorova O.A., Shepel’ N.E., Gromov S.P., Alfimov M.V., Kuz’mina L.G., Howard J.A., Saltiel J.
Russian Chemical Bulletin ,
2005
39.
39
V. F. Gachkovskii
Biofizika ,
1959
40.
Strehmel B., Henbest K.B., Sarker A.M., Malpert J.H., Chen D.Y., Rodgers M.A., Neckersa D.C.
Journal of Nanoscience and Nanotechnology ,
2001
41.
Bis(azacrown ether) and bis(benzocrown ether) dyes: butterflies, tweezers and rods in cation binding
Fery-Forgues S., Al-Ali F.
Journal of Photochemistry and Photobiology C: Photochemistry Reviews ,
2004
42.
Vedernikov A.I., Ushakov E.N., Lobova N.A., Kiselev A.A., Alfimov M.V., Gromov S.P.
Russian Chemical Bulletin ,
2005
43.
43
N. Bunge
Ber. Deutsch. Chem. Ges. ,
1870
44.
Vedernikov Artem Igorevich, Lobova Natalia Anatol'evna, Ushakov Evgeny Nikolaevich, Alfimov Mikhail Vladimirovich, Gromov Sergei Panteleimonovich
Mendeleev Communications ,
2005
45.
Gromov S.P., Vedernikov A.I., Kuz’mina L.G., Lobova N.A., Basok S.S., Strelenko Y.A., Alfimov M.V.
Russian Chemical Bulletin ,
2009
46.
Shinkai S., Yoshida T., Miyazaki K., Manabe O.
Bulletin of the Chemical Society of Japan ,
1987
47.
Vedernikov Artem Igorevich, Sazonov Sergey Konstantinovich, Loginov Pavel S, Lobova Natalia Anatol'evna, Alfimov Mikhail Vladimirovich, Gromov Sergei Panteleimonovich
Mendeleev Communications ,
2007
48.
Vedernikov A.I., Sazonov S.K., Kuz’mina L.G., Howard J.A., Alfimov M.V., Gromov S.P.
Russian Chemical Bulletin ,
2009
49.
50
G. Glacomello
Gazzetta. ,
1935
50.
Gromov S.P., Ushakov E.N., Vedernikov A.I., Lobova N.A., Alfimov M.V., Strelenko Y.A., Whitesell J.K., Fox M.A.
Organic Letters ,
1999
51.
Self-organization of highly stable electron donor - Acceptor complexes via host - Guest interactions
Ushakov E.N., Gromov S.P., Vedernikov A.I., Malysheva E.V., Botsmanova A.A., Alfimov M.V., Eliasson B., Edlund U.G., Whitesell J.K., Fox M.A.
Journal of Physical Chemistry A ,
2001
52.
Gromov S.P., Vedernikov A.I., Ushakov E.N., Lobova N.A., Botsmanova A.A., Kuz’mina L.G., Churakov A.V., Strelenko Y.A., Alfimov M.V., Howard J.A., Johnels D., Edlund U.G.
New Journal of Chemistry ,
2005
53.
Vedernikov Artem Igorevich, Kuz'mina Ludmila G, Lobova Natalia Anatol'evna, Ushakov Evgeny Nikolaevich, Howard Judith A. K., Alfimov Mikhail Vladimirovich, Gromov Sergei Panteleimonovich
Mendeleev Communications ,
2007
54.
Ushakov E.N., Nadtochenko V.A., Gromov S.P., Vedernikov A.I., Lobova N.A., Alfimov M.V., Gostev F.E., Petrukhin A.N., Sarkisov O.M.
Chemical Physics ,
2004
55.
Vilar R.
Angewandte Chemie - International Edition ,
2003
56.
Kato Y., Nishizawa S., Teramae N.
Organic Letters ,
2002
57.
Mori K., Murai O., Hashimoto S., Nakamura Y.
Tetrahedron Letters ,
1996
58.
MacGillivray L.R.
Journal of Organic Chemistry ,
2008
59.
Gao X., Friščić T., MacGillivray L.R.
Angewandte Chemie - International Edition ,
2004
60.
Kelly T.R., Zhao C., Bridger G.J.
Journal of the American Chemical Society ,
1989
61.
Kelly T.R., Bridger G.J., Zhao C.
Journal of the American Chemical Society ,
1990
62.
Bassani D.M., Darcos V., Mahony S., Desvergne J.
Journal of the American Chemical Society ,
2000
63.
Bassani D.M., Sallenave X., Darcos V., Desvergne J.
Chemical Communications ,
2001
64.
Darcos V., Griffith K., Sallenave X., Desvergne J., Guyard-Duhayon C., Hasenknopf B., Bassani D.M.
Photochemical and Photobiological Sciences ,
2003
65.
Skene W.G., Couzigné E., Lehn J.
Chemistry - A European Journal ,
2003
66.
Skene W.G., Berl V., Risler H., Khoury R., Lehn J.
Organic and Biomolecular Chemistry ,
2006
67.
Coote S.C., Bach T.
Journal of the American Chemical Society ,
2013
68.
Mayr F., Wiegand C., Bach T.
Chemical Communications ,
2014
69.
Yanagisawa Y., Nishiyama Y., Tanimoto H., Morimoto T., Kakiuchi K.
Tetrahedron Letters ,
2014
70.
Tanaka K., Fujiwara T.
Organic Letters ,
2005
71.
Vida Pol Y., Suau R., Perez-Inestrosa E., Bassani D.M.
Chemical Communications ,
2004
72.
Fedorova O., Fedorov Y.V., Gulakova E., Schepel N., Alfimov M., Goli U., Saltiel J.
Photochemical and Photobiological Sciences ,
2007
73.
Rivera J.M., Silva-Brenes D.
Organic Letters ,
2013
74.
Ramamurthy V., Parthasarathy A.
Israel Journal of Chemistry ,
2011
75.
Vallavoju N., Sivaguru J.
Chemical Society Reviews ,
2014
76.
Szejtli J.
Chemical Reviews ,
1998
77.
Wang H.M., Wenz G.
Beilstein Journal of Organic Chemistry ,
2013
78.
Utsuki T., Hirayama F., Uekama K.
Journal of the Chemical Society Perkin Transactions 2 ,
1993
79.
Herrmann W., Wehrle S., Wenz G.
Chemical Communications ,
1997
80.
Kaliappan R., Maddipatla M.V., Kaanumalle L.S., Ramamurthy V.
Photochemical and Photobiological Sciences ,
2007
81.
Wang H.M., Wenz G.
Chemistry - An Asian Journal ,
2011
82.
Unique catalytic effect of a cyclodextrin host on photodimerization of coumarin in nonpolar solvents
Asahara H., Iwamoto T., Kida T., Akashi M.
Tetrahedron Letters ,
2013
83.
Lee J.W., Samal S., Selvapalam N., Kim H., Kim K.
Accounts of Chemical Research ,
2003
84.
Assaf K.I., Nau W.M.
Chemical Society Reviews ,
2015
85.
Jon S.Y., Ko Y.H., Park S.H., Kim H., Kim K.
Chemical Communications ,
2001
86.
Pattabiraman M., Natarajan A., Kaliappan R., Mague J.T., Ramamurthy V.
Chemical Communications ,
2005
87.
Pattabiraman M., Natarajan A., Kaanumalle L.S., Ramamurthy V.
Organic Letters ,
2005
88.
Pattabiraman M., Kaanumalle L.S., Natarajan A., Ramamurthy V.
Langmuir ,
2006
89.
Mitkina T.V., Naumov D.Y., Kurat’eva N.V., Gerasko O.A., Fedin V.P.
Russian Chemical Bulletin ,
2006
90.
91
L. M. Vorob'eva
Biokhimiya ,
1956
91.
Maddipatla M.V., Kaanumalle L.S., Natarajan A., Pattabiraman M., Ramamurthy V.
Langmuir ,
2007
92.
Barooah N., Pemberton B.C., Johnson A.C., Sivaguru J.
Photochemical and Photobiological Sciences ,
2008
93.
Barooah N., Pemberton B.C., Sivaguru J.
Organic Letters ,
2008
94.
Pemberton B.C., Barooah N., Srivatsava D.K., Sivaguru J.
Chemical Communications ,
2010
95.
Gromov S.P., Vedernikov A.I., Kuz'mina L.G., Kondratuk D.V., Sazonov S.K., Strelenko Y.A., Alfimov M.V., Howard J.A.
European Journal of Organic Chemistry ,
2010
96.
Pemberton B.C., Singh R.K., Johnson A.C., Jockusch S., Da Silva J.P., Ugrinov A., Turro N.J., Srivastava D.K., Sivaguru J.
Chemical Communications ,
2011
97.
Regiospecific [2 + 2] photocyclodimerization of trans-4-styrylpyridines templated by cucurbit[8]uril
Nakamura A., Irie H., Hara S., Sugawara M., Yamada S.
Photochemical and Photobiological Sciences ,
2011
98.
Ivanov D.A., Petrov N.K., Alfimov M.V., Vedernikov A.I., Gromov S.P.
High Energy Chemistry ,
2014
99.
100
V. V. Zolotarev
Chem. Abs. ,
1941
100.
Maddipatla M.V., Pattabiraman M., Natarajan A., Srivastav K., Mague J.T., Ramamurthy V.
Organic and Biomolecular Chemistry ,
2012
101.
102.
Kaliappan R., Kaanumalle L.S., Natarajan A., Ramamurthy V.
Photochemical and Photobiological Sciences ,
2006
103.
Gibb C.L., Gibb B.C.
Journal of the American Chemical Society ,
2004
104.
Jayaraj N., Zhao Y., Parthasarathy A., Porel M., Liu R.S., Ramamurthy V.
Langmuir ,
2009
105.
Kaanumalle L.S., Ramamurthy V.
Chemical Communications ,
2007
106.
Parthasarathy A., Kaanumalle L.S., Ramamurthy V.
Organic Letters ,
2007
107.
Parthasarathy A., Samanta S.R., Ramamurthy V.
Research on Chemical Intermediates ,
2012
108.
Jagadesan P., Mondal B., Parthasarathy A., Rao V.J., Ramamurthy V.
Organic Letters ,
2013
109.
Fujita M., Oguro D., Miyazawa M., Oka H., Yamaguchi K., Ogura K.
Nature ,
1995
110.
10.1002/1521-3773(20020415)41:8<1347::AID-ANIE1347>3.0.CO;2-X
111.
Karthikeyan S., Ramamurthy V.
Tetrahedron Letters ,
2005
112.
Karthikeyan S., Ramamurthy V.
Journal of Organic Chemistry ,
2006
113.
Karthikeyan S., Ramamurthy V.
Journal of Organic Chemistry ,
2006
114.
10.1021/ja020718+
115.
Nishioka Y., Yamaguchi T., Yoshizawa M., Fujita M.
Journal of the American Chemical Society ,
2007
116.
Nishioka Y., Yamaguchi T., Kawano M., Fujita M.
Journal of the American Chemical Society ,
2008
117.
Horiuchi S., Nishioka Y., Murase T., Fujita M.
Chemical Communications ,
2010
118.
Murase T., Peschard S., Horiuchi S., Nishioka Y., Fujita M.
Supramolecular Chemistry ,
2011
119.
Murase T., Nishijima Y., Fujita M.
Chemistry - An Asian Journal ,
2012