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Sulfonyl‐Activated Cyclobutenes as Building Blocks for the Synthesis of Dihydrodiazepines
Author(s) -
Landen Harald,
Martin HansDieter,
Steigel Alois
Publication year - 1987
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19871200208
Subject(s) - sulfone , chemistry , sulfoxide , cyclobutene , regioselectivity , yield (engineering) , reactivity (psychology) , sodium periodate , sulfonyl , medicinal chemistry , organic chemistry , catalysis , ring (chemistry) , medicine , materials science , alternative medicine , alkyl , pathology , metallurgy
1,2‐Bis(phenylthio)‐1‐cyclobutene ( 5 ), prepared in high yield using a modified literature procedure, was oxidized to the corresponding bis‐sulfone 2 , sulfone‐sulfoxide 9 , bis‐sulfoxide 10 , or monosulfoxide 15 by means of hydrogen peroxide or sodium periodate, respectively. When treated with diazomethane the bis‐sulfone 2 and the sulfone‐sulfoxide 9 yield the dihydrodiazepines 4a and 11 , respectively. The reactivity of these cyclobutenes and the regioselectivity of 9 is discussed in terms of the MNDO model.