Abstract
New calix[4]resorcinols containing four organochlorine moieties have been synthesized in high yields via one-step condensation of resorcinol, 2-methylresorcinol or pyrogallol with 4′-formylphenyl 4-(chloromethyl)benzoate. It has been found that the diastereomeric ratio of the products depends substantially on the starting polyphenol. The rctt- and/or rccc-diastereomers have been isolated and their structure and composition have been determined by 1H, 13C NMR and IR spectroscopy, MALDI mass spectrometry and elemental analysis, the crystal structure of one rctt-product has been established by single crystal X-ray diffraction.
References
1.
Sémeril D., Matt D.
Coordination Chemistry Reviews,
2014
2.
Knyazeva I.R., Burilov A.R., Pudovik M.A., Habicher W.D.
Russian Chemical Reviews,
2013
3.
Clark T.E., Makha M., Sobolev A.N., Su D., Rohrs H., Gross M.L., Atwood J.L., Raston C.L.
New Journal of Chemistry,
2008
4.
Solovyov A.V., Cherenok S.O., Kalchenko O.I., Atamas L.I., Kazantseva Z.I., Koshets I.A., Tsymbal I.F., Kalchenko V.I.
Journal of Molecular Liquids,
2011
5.
Kalchenko O., Marcinowicz A., Poznanski J., Cherenok S., Solovyov A., Zielenkiewicz W., Kalchenko V.
Journal of Physical Organic Chemistry,
2005
6.
Hoegberg A.G.
Journal of Organic Chemistry,
1980
7.
Tunstad L.M., Tucker J.A., Dalcanale E., Weiser J., Bryant J.A., Sherman J.C., Helgeson R.C., Knobler C.B., Cram D.J.
Journal of Organic Chemistry,
1989
8.
Yamakawa Y., Ueda M., Nagahata R., Takeuchi K., Asai M.
Journal of the Chemical Society Perkin Transactions 1,
1998
9.
Prosvirkin A.V., Kazakova E.K., Gubaidullin A.T., Litvinov I.A., Gruner M., Habicher W.D., Konovalov A.I.
Russian Chemical Bulletin,
2005
10.
Knyazeva I.R., Sokolova V.I., Gruner M., Habicher W.D., Syakaev V.V., Khrizanforova V.V., Gabidullin B.M., Gubaidullin A.T., Budnikova Y.H., Burilov A.R., Pudovik M.A.
Tetrahedron Letters,
2013
11.
Knyazeva I.R., Mukhamedyanova K.M., Syakaev V.V., Gubaidullin A.T., Habicher W.D., Burilov A.R.
Tetrahedron Letters,
2018