Onium Ions. 26. Aminodiazonium Ions: Preparation, 1H, 13C, and 15N NMR Structural Studies, and Electrophilic Amination of Aromatics

Alfred Mertens; Koop Lammertsma; Massoud Arvanaghi; George A. Olah

doi:10.1021/ja00355a023

Onium Ions. 26. Aminodiazonium Ions: Preparation, ¹H, ¹³C, and ¹⁵N NMR Structural Studies, and Electrophilic Amination of Aromatics

Alfred Mertens, Koop Lammertsma, Massoud Arvanaghi, George A. Olah

University of Southern California

Research output: Contribution to journal › Article › peer-review

61 Citations (Scopus)

Abstract

Protonation of hydrazoic acid and alkyl azides with FSO₃H/SbF₅, HF/SbF₅, or HF/BF₃ results in the formation of stable aminodiazonium ions as shown by ¹H, ¹³C, and ¹⁵N NMR spectroscopic studies. Molecular orbital calculations of the thermodynamics of the protonation of hydrazoic acid also support preferential formation of the aminodiazonium ion. The aminodiazonium ion was also prepared in situ from NaN₃/AlCl₃/HCl or (CH₃)₃SiN₃/AlCl₃/HCl [(CH₃)₃SiN₃/HF/BF₃]. Aminodiazonium salts were found to affect electrophilic amination of aromatics in high yields, with generally high regioselectivity and low substrate selectivity.

Original language	English
Pages (from-to)	5657-5660
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	105
Issue number	17
DOIs	https://doi.org/10.1021/ja00355a023
Publication status	Published - Aug 1983
Externally published	Yes

ASJC Scopus subject areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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abstract = "Protonation of hydrazoic acid and alkyl azides with FSO3H/SbF5, HF/SbF5, or HF/BF3 results in the formation of stable aminodiazonium ions as shown by 1H, 13C, and 15N NMR spectroscopic studies. Molecular orbital calculations of the thermodynamics of the protonation of hydrazoic acid also support preferential formation of the aminodiazonium ion. The aminodiazonium ion was also prepared in situ from NaN3/AlCl3/HCl or (CH3)3SiN3/AlCl3/HCl [(CH3)3SiN3/HF/BF3]. Aminodiazonium salts were found to affect electrophilic amination of aromatics in high yields, with generally high regioselectivity and low substrate selectivity.",

author = "Alfred Mertens and Koop Lammertsma and Massoud Arvanaghi and Olah, {George A.}",

year = "1983",

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T1 - Onium Ions. 26. Aminodiazonium Ions

T2 - Preparation, 1H, 13C, and 15N NMR Structural Studies, and Electrophilic Amination of Aromatics

AU - Mertens, Alfred

AU - Lammertsma, Koop

AU - Arvanaghi, Massoud

AU - Olah, George A.

PY - 1983/8

Y1 - 1983/8

N2 - Protonation of hydrazoic acid and alkyl azides with FSO3H/SbF5, HF/SbF5, or HF/BF3 results in the formation of stable aminodiazonium ions as shown by 1H, 13C, and 15N NMR spectroscopic studies. Molecular orbital calculations of the thermodynamics of the protonation of hydrazoic acid also support preferential formation of the aminodiazonium ion. The aminodiazonium ion was also prepared in situ from NaN3/AlCl3/HCl or (CH3)3SiN3/AlCl3/HCl [(CH3)3SiN3/HF/BF3]. Aminodiazonium salts were found to affect electrophilic amination of aromatics in high yields, with generally high regioselectivity and low substrate selectivity.

AB - Protonation of hydrazoic acid and alkyl azides with FSO3H/SbF5, HF/SbF5, or HF/BF3 results in the formation of stable aminodiazonium ions as shown by 1H, 13C, and 15N NMR spectroscopic studies. Molecular orbital calculations of the thermodynamics of the protonation of hydrazoic acid also support preferential formation of the aminodiazonium ion. The aminodiazonium ion was also prepared in situ from NaN3/AlCl3/HCl or (CH3)3SiN3/AlCl3/HCl [(CH3)3SiN3/HF/BF3]. Aminodiazonium salts were found to affect electrophilic amination of aromatics in high yields, with generally high regioselectivity and low substrate selectivity.

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Onium Ions. 26. Aminodiazonium Ions: Preparation, ¹H, ¹³C, and ¹⁵N NMR Structural Studies, and Electrophilic Amination of Aromatics

Abstract

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