Ralph, Matthew S.

Roesner, Faculty Advisor, Rebecca

Digital Commons @ Illinois Wesleyan University

Illinois Wesleyan UniversityDigital Commons @ IWUJohn Wesley Powell Student ResearchConference 2003, 14th Annual JWP ConferenceApr 12th, 1:15 PM - 2:15 PMThe Synthesis and Isolation of Mono-BOC-Protected 1,4-Phenylene Diamine and FurtherReaction with HexamolybdateMatthew S. RalphIllinois Wesleyan UniversityRebecca Roesner, Faculty AdvisorIllinois Wesleyan UniversityFollow this and additional works at: http://digitalcommons.iwu.edu/jwprcThis Event is brought to you for free and open access by The Ames Library, the Andrew W. Mellon Center for Curricular and FacultyDevelopment, the Office of the Provost and the Office of the President. It has been accepted for inclusion in Digital Commons @ IWU bythe faculty at Illinois Wesleyan University. For more information, please contact digitalcommons@iwu.edu.©Copyright is owned by the author of this document.Matthew S. Ralph and Rebecca Roesner, Faculty Advisor, "The Synthesis and Isolation of Mono-BOC-Protected1,4-Phenylene Diamine and Further Reaction with Hexamolybdate" (April 12, 2003). John Wesley Powell Student ResearchConference. Paper 9.http://digitalcommons.iwu.edu/jwprc/2003/posters2/9THE JOHN WESLEY POWELL SnJDENI RESEARCH CONFERENCE - APRIl, 2003 Poster Presentation P34 THE SYNTHESIS AND ISOLATION OF MONO-ROC-PROTECTED 1,4-PHENYLENE DIAMINE AND FURTHER REACTION WITH HEXAMOLYBDATE Matthew S, Ralph and Rebecca A. Roesner* Department ofChernistry, Illinois Wesleyan University When reacting unprotected diamines with polyoxylmetalates, a mixture of di-, mono-, and unsubstituted products is obtained, A simple aromatic diamine, 1 ,4-phenylene diamine, was used to investigate a method through which a mono-BOC-protected diamine could be synthesized and isolated for further reaction with the hexamolybdate ion to obtain a mono-substituted product. The 1 ,4-phenylene diamine was purified by sublimation and the purified diamine was then reacted in a 1 :  1 mole ratio with di-tert­butyl dicarbonate to mono-protect the diamine, According to GC-Mass Spectrometry, the acetonitrile-soluble products of this reaction were 97.7% mono-protected and 2.0% di-protected. The mono-protected product was then purified via column chromatography with final percent yields of 89.1 % and 8 1 .5% in two trials. Purity was verified by GC­Mass Spectrometry and H-NMR. The mono-protected 1 ,4-phenylene diamine was reacted with the hexamolybdate ion to yield a mono-substituted 1 ,4-phenylene diamine. 

The Synthesis and Isolation of Mono-BOC-Protected 1,4-Phenylene Diamine and Further Reaction with Hexamolybdate

http://digitalcommons.iwu.edu/cgi/viewcontent.cgi?article=2022&context=jwprc

The Synthesis and Isolation of Mono-BOC-Protected 1,4-Phenylene Diamine and Further Reaction with Hexamolybdate

Abstract

Similar works

Full text

Available Versions

Digital Commons @ Illinois Wesleyan University