Item – Theses Canada

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OCLC number
80431504
Link(s) to full text
LAC copy
LAC copy
Author
Jones, Christopher Charles Victor,1978-
Title
Synthesis of 2,7-disubstituted N, N-diethyl naphthalene-1,8-dicarboxamide derivatives by directed ortho metalation-cross coupling methodology.
Degree
M. Sc. -- Queen's University, 2005
Publisher
Ottawa : Library and Archives Canada = Bibliothèque et Archives Canada, [2006]
Description
2 microfiches
Notes
Includes bibliographical references.
Abstract
Directed 'ortho' Metalation (D'o'M) of the readily prepared 'N,N'-diethyl naphthalene-1,8-dicarboxamide leads, after electrophilic quench, to 2- and 2,7-substituted 'N,N'-diethyl naphthalene-1,8-dicarboxamide products as a function of the conditions. When the 2 and 2,7 substituents are halogens ('N,N'-diethyl-2-iodonaphthalene-1,8-dicarboxamide, ' N,N'-diethyl-2,7-dibromonaphthalene-1,8-dicarboxamide, ' N,N'-diethyl-2,7-diiodonaphthalene-1,8-dicarboxamide, Suzuki-Miyaura Pd-catalyzed cross coupling methodology was employed to form 2-aryl and 2,7-diaryl-' N,N'-diethyl naphthalene-1,8-dicarboxamides. Treatment of ' N,N'-diethyl-2,7-diphenylnaphthalene-1,8-dicarboxamide leads to the mono fluorenone of 'N,N'-diethyl-2,7-diphenylnaphthalene-1,8-dicarboxamide by a Directed remote Metalation (DreM) reaction. The scope and limitations of these methodologies are presented. Different ratios of 2- and 2,7-deuterated products are obtained as a function of conditions and these results are discussed. Rotational barriers of the C-Ar bond rotation have been determined for N,N-diethyl naphthalene-1,8-dicarboxamide using VT NMR. The X-ray structure of ' N,N'-diethyl-2,7-bis(trimethylsilanyl)naphthalene-1,8-dicarboxamide is presented.
ISBN
0494050381
9780494050385