Theoretical Studies on the Intramolecular Cyclization of (Z)-8-(Trimethylstannyl)oct-6-enal

Abstract

Abstract: The intramolecular cyclization of (Z)-8-(trimethylstannyl)oct-6-enal were studied by using the density functional method at the B3LYP/6-31G^*level.The structures and energies of the stationary points were calculated to produce the activation barriers.The transition states were testified by using vibration analysis and IRC calculations.Three reaction pathways were analyzed.All the reactions are the exothermic reations and the concerted reaction processes which have only one double-six-membered transition state dominated by the Cl-C6 vibration.Each of the reactions progresses with the bond formation of Sn10-O9 and C1-C6, the bond breaking of C8-Sn10 and the migration of the diene double bond to form the six-membered cyclic product.The results show that the reaction occurs with a high stereoselectivity.The product, in which both-OSn(CH₃)₃and-C₂H₃moieties are at the equatorial position, is the most stable one among three reactions, whereas the mainly product is obtained through the double-six-membered chairlike conformational transition state with the lowest barrier height.ThiSISIn excellent {agreement} with the experimental results.

Key words: (Z)-8-(Trimethylstannyl)oct-6-enal, Cyclization, Stereoselectivity, B3LYP

CLC Number:

O641

TrendMD:

XU Kai-Lai, XIE Dai-Qian, YAN Guo-Sen . Theoretical Studies on the Intramolecular Cyclization of (Z)-8-(Trimethylstannyl)oct-6-enal[J]. Chem. J. Chinese Universities, 2003, 24(11): 2031.

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Theoretical Studies on the Intramolecular Cyclization of (Z)-8-(Trimethylstannyl)oct-6-enal

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