Abstract
The configurational stability of compounds 1–4 has been confirmed by NMR spectroscopy and chiral chromatography (analytical separation of enantiomers 1 and 2); the antiaromatic (4n) destabilisation of the planar transition state of enantiomerisation is discussed.
References
1.
10.1070/MC2003v013n06ABEH001749_bib1
Eliel
Stereochemistry of Organic Compounds,
1994
2.
10.1070/MC2003v013n06ABEH001749_bib2_1
Bell
J. Chem. Soc.,
1952
3.
Mislow K., Glass M.A., O'Brien R.E., Rutkin P., Steinberg D.H., Weiss J., Djerassi C.
Journal of the American Chemical Society,
1962
4.
Hall D.M., Insole J.M.
Journal of the Chemical Society (Resumed),
1964
5.
10.1070/MC2003v013n06ABEH001749_bib2_4
Insole
J. Chem. Soc. (C),
1971
6.
Allinger N.L., Szkrybalo W., DaRooge M.A.
Journal of Organic Chemistry,
1963
7.
Müllen K., Heinz W., Klärner F., Roth W.R., Kindermann I., Adamczak O., Wette M., Lex J.
Chemische Berichte,
1990
8.
Rashidi-Ranjbar P., Sandström J.
Tetrahedron Letters,
1987
9.
Mislow K., Perlmutter H.D.
Journal of the American Chemical Society,
1962
10.
10.1070/MC2003v013n06ABEH001749_bib5
Olszewska
Book of Abstracts of the 7th International Conference on Circular Dichroism,
1999
11.
Kwit M., Rychlewska U., Gawroński J.
New Journal of Chemistry,
2002
12.
10.1070/MC2003v013n06ABEH001749_bib7
Sako
Mem. Coll. Eng. Kyushu Imp. Univ.,
1932
13.
Reisinger A., Koch R., Wentrup C.
Journal of the Chemical Society Perkin Transactions 1,
1998
14.
Von Niementowski S.
Berichte der deutschen chemischen Gesellschaft,
1901
15.
Ried W., Storbeck W.
Chemische Berichte,
1962
16.
Bakibaev A.A., Yagovkin A.Y., Vostretsov S.N.
Russian Chemical Reviews,
1998