Naphthalene tetrachlorides and related compounds. Part 7. Products of methanolysis of a 1-p-tolylnaphthalene tetrachloride; evidence for a rapid bimolecular elimination of methanol from the 2,3-dichloro-1-methoxy-1-p-tolyl-1,2-dihydronaphthalenes

Autor:	Keith R. Bedford, Peter B. D. de la Mare
Rok vydání:	1979
Předmět:	chemistry.chemical_compound chemistry Tetrachloride Methanol Photochemistry Medicinal chemistry Spectral line Naphthalene E1cB-elimination reaction
Zdroj:	Journal of the Chemical Society, Perkin Transactions 2. :82
ISSN:	1364-5471 0300-9580
DOI:	10.1039/p29790000082
Popis:	Unimolecular methanolysis of r-1,c-2,t-3,t-4-tetrachloro-1-p-tolyltetralin gives two isomeric 1-methoxy-1-p-tolyl-2,3,4-trichlorotetralins, each of which undergoes bimolecular elimination in two defined stages having similar rates, and giving 2,3-dichloro-1-p-tolylnaphthalene as the nearly exclusive final product. The intermediate 2,3-dichloro-1-methoxy-1-p-tolyl-1,2-dihydronaphthalenes, which can be characterised through signals in their 1H n.m.r. spectra, must, therefore, undergo bimolecular elimination of methanol at rates which can be estimated from the rates of build-up of their precursors. The theoretical implications of these results are discussed; it is suggested that this elimination must be far on the E1cb side of the spectrum of bimolecular eliminations.
Databáze:	OpenAIRE
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