AM1 semi-empirical SCF MO calculations for the structure optimization and configurational properties of cyclonona-1,2,4,5,7,8-hexaene 3, its hexamethyl derivative 4 and cyclododeca-1,2,5,6,9,10-hexaene 5 show that the combination of three allenic units of the same chirality yields an enantiomeric pair which is the most stable configuration of 3, 4 and 5.
References
1.
AnetF. A. L., and GhiaciM., J. Am. Chem. Soc., 1980, 102, 2528 and references cited therein.
2.
GarrattP. J., Aromaticity, Wiley-Interscience, New York, 1986.
3.
JohnsonR. P., Chem. Rev., 1989, 89, 1111.
4.
GreenbergA., and LiebmanJ. F., Strained Organic Molecules, Academic Press, New York, 1978; K. B. Wiberg, Angew. Chem., Int. Ed. Engl., 1986, 25, 312.
5.
StewartJ. J. P., J. Comput-Aided Mol. Des., 1990, 4, 1.
6.
HirstD. M., A Computational Approach to Chemistry, Blackwell Scientific Publications, Oxford, 1990.
7.
Serena Software, Box 3076, Bloomington, IN, USA.
8.
DewarM. J. S., ZeobishE. G., HealyE. F., and StewartJ. J. P., J. Am. Chem. Soc., 1985, 107, 3907.
9.
J. J. P. Stewart, QCPE 581, Department of Chemistry, Indiana University, Bloomington, IN, USA.
10.
DewarM. J. S., HealyE. F., and StewartJ. J. P., J. Chem. Soc., Faraday Trans., 1984, 80, 227.
WinsteinS., J. Am. Chem. Soc., 1959, 81, 6524; L. A. Paquette, Angew. Chem., Int. Ed. Engl., 1978, 17, 106; R. Gleiter and W. Schäfer, Acc. Chem. Res., 1990, 23, 369.
