The Theory and Synthesis of [2.2.2] Propellane

Author

Theodore Mark Prociv, The Graduate Center, City University of New YorkFollow

Date of Degree

1983

Document Type

Dissertation

Degree Name

Ph.D.

Program

Chemistry

Advisor

Joseph J. Dannenberg

Committee Members

R. Odum

L. Massa

James Howell

Subject Categories

Chemistry

Abstract

INDO calculations indicated that the triplet state of dimethylene cyclohexane could rearrange to gometrically relaxed triplets which should collapse preferentially to the ground state [2.2.2] Propellane. A mercury sensitized photolysis of the dimethylene cyclohexane did in fact result in detectable quantities of the propellane, trapped as 1,4 dibromobicyclo octane. Synthesis of 1,4 dibromobicyclo octane and 1,1,6,6 tetradeuterodimethylene-cyclohexane are presented in the dissertation. Included in the dissertation are the results of INDO calculations of various propellane isomers having nitrogens and borons in the bridgehead positions.

Comments

Digital reproduction from the UMI microform.

Recommended Citation

Prociv, Theodore Mark, "The Theory and Synthesis of [2.2.2] Propellane" (1983). CUNY Academic Works.
https://academicworks.cuny.edu/gc_etds/4125