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Halocarbenes as diagnostic tools for mass spectral localization of double bonds
Author(s) -
Schuerch Stefan,
Howald Markus,
Gfeller Hans,
Schlunegger Urs Peter
Publication year - 1994
Publication title -
rapid communications in mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.528
H-Index - 136
eISSN - 1097-0231
pISSN - 0951-4198
DOI - 10.1002/rcm.1290080305
Subject(s) - chemistry , double bond , fragmentation (computing) , cycloaddition , yield (engineering) , adduct , alkyl , bromine , mass spectrometry , mass spectrum , computational chemistry , photochemistry , organic chemistry , chromatography , catalysis , computer science , metallurgy , operating system , materials science
Different halocyclopropanes prepared by cycloaddition of halocarbenes to olefins by phase‐transfer reactions have been analyzed by gas chromatography/mass spectrometry (GC/MS). Starting from CCl 2 ‐adducts, the investigations have been extended to bromine‐ and fluorine‐containing cyclopropanes. As reaction partners, a group of olefins, containing different alkyl substituents, have been selected. Thereby, special attention has been paid to smooth reaction conditions, high reaction yield and simple handling. The suitability for mass spectral analysis is discussed. Fragmentation pathways and diagnostic potential are evaluated. Best results have been obtained by addition of bromofluorocarbene to double bonds. The resulting bromofluorocyclopropanes are considered to be the most promising derivatives for mass spectral localization of double bonds.