Date of Award
2005
Document Type
Honors Thesis (Open Access)
Department
Colby College. Chemistry Dept.
Advisor(s)
Dasan M. Thamattoor
Second Advisor
Jeffrey L. Katz
Abstract
2-methoxy-2-methylpropylidene was photochemically generated from a non-nitrogenous precursor, 1a,9b-Dihydro-IH-cyclopropa[1]phenanthrene-l-etbane 2-methoxy-2-methyl, available in two steps from phenanthrene. Two competing rearrangement pathways were observed for the p-methoxy carbene, 1,2-methyl shift and C-H insertion, which had varying weights depending on the solvent used. Nevertheless, the C-H insertion was always predominant, contrary to the current understanding of B-substituted carbenes, which apparently needs revision. An attempt was also made to measure by LFP the rate constant of rearrangement and lifetime of the stabilized l-chloro-2-methoxy-2-metbylpropylidene.
Keywords
Carbenes (Methylene compounds), Photochemistry, Organic compounds -- Synthesis, 2-methoxy-2-methylpropylidene
Recommended Citation
Presolski, Stanislav, "Photochemical generation of 2-methoxy-2methylpropylidene and its rearrangement pathways" (2005). Honors Theses. Paper 201.https://digitalcommons.colby.edu/honorstheses/201
Copyright
Colby College theses are protected by copyright. They may be viewed or downloaded from this site for the purposes of research and scholarship. Reproduction or distribution for commercial purposes is prohibited without written permission of the author.
