Synthesis and 13C NMR Spectroscopy of 13C-Labeled α,ω-Diphenylpolyynes

Rik R. Tykwinski; Thanh Luu

doi:10.1055/s-0031-1290983

Synthesis, Table of Contents

Synthesis 2012; 44(12): 1915-1922
DOI: 10.1055/s-0031-1290983

paper

Synthesis and ¹³C NMR Spectroscopy of ¹³C-Labeled α,ω-Diphenylpolyynes

Rik R. Tykwinski*

^aDepartment of Chemistry and Pharmacy and Interdisciplinary Center of Molecular Materials (ICMM), University of Erlangen-Nuremberg, Henkestr. 42, 91054 Erlangen, Germany

,

Thanh Luu

^bDepartment of Chemistry, University of Alberta, Edmonton, AB, T6G 2G2, Canada, Email: rik.tykwinski@chemie.uni-erlangen.de

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Abstract

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Dedicated to Dr. Tom Nakashima for a lifelong commitment to NMR spectroscopy

Abstract

The synthesis of three ¹³C-labeled α,ω-diphenylpolyynes is described. The known positions of the labeled carbon atoms allow assignment of the resonances in the ¹³C NMR spectra and identification of trends in the chemical shifts.

Key words

alkynes - carbenes - ¹³C labeling - polyynes - Fritsch–Buttenberg–Wiechell rearrangement

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References

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24 The syntheses of unlabeled Ph[3] and Ph[4] were analogous to those reported herein for the labeled compounds. Unlabeled Ph[4], Ph[6], and Ph[8] were synthesized as reported in reference 3d. The synthesis of unlabeled Ph[5] has been reported (see references 3b and 3e) and is also described in the Supporting Information
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Supplementary Material

Supporting Information