A new general fragmentation reaction in mass spectrometry: The hydrogen-carbon, carbon-carbon double rearrangement of 2 heteroalkyl substituted diphenylmethyl cations

Eur. J. Mass Spectrom. 1, 73–79 (1995)
DOI: 10.1255/ejms.162

A new general fragmentation reaction in mass spectrometry: The hydrogen-carbon, carbon-carbon double rearrangement of 2 heteroalkyl substituted diphenylmethyl cations

Maria Concetta Natoli
Dipartimento di Chimica Organica, via Archirafi 20, I-90123 Palermo, Italy
Pasquale Agozzino, Leopoldo Ceraulo,^* Mirella Ferrugia and Liliana Lamartina
Dipartimento di Chimica e Tecnologie Farmaceutiche, via Archirafi 32, I-90123 Palermo, Italy

ABSTRACT:

Diphenylmethyl cations formed by benzylic cleavage of the molecular ions of ortho heteroalkyl substituted 1,1 diphenylalkanes undergo the double rearrangement process (H to C followed by C to C) previously reported for ortho-methoxy derivatives. Hence the formation of substituted benzyl (or tropylium) ions allowing this double rearrangement process constitutes an interesting type of fragmentation reaction characteristic for 1,1 diphenylalkanes bearing ortho substituents (OMe, OEt, OiPr, SMe, NHMe, NMe2) which are able to transfer a hydride to the charged benzyl carbon of diphenylmethyl cations formed bybenzylic cleavage of the molecular ion.

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