Date of Award

2016

Document Type

Honors Thesis (Open Access)

Department

Colby College. Chemistry Dept.

Advisor(s)

Dasan Thamattoor

Second Advisor

Nicholas Boekelheide

Abstract

The twisted and sterically hindered 4,5-dibromophenanthrene, was synthesized from 2,6-dibromoiodobenzene in a four-step pathway, or from 1,3-dibromobenzene in a three-step pathway. Then, 4,5-dibromophenanthrene was subjected to a Kumada coupling, leading to the synthesis of an even more twisted 4-bromo-5-tert-butylphenanthrene. Computational studies using density functional theory were performed to compare experimental and theoretical characteristics of these compounds, such as dihedral angles, optimized structures, and transition state energy barriers.

The purpose of these experiments is to fill gaps in chemical databases, synthesize more pronounced twists in normally planar phenanthrene molecules, and to ultimately synthesize 4,5-bis-tert-butylphenanthrene, which may have interesting spectral results due to the close proximity of its substituent tert-butyl groups.

Keywords

twisted phenanthrene, tert-butyl, Kumada coupling, dihedral angles, enantiomeric interconversion

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