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Synthesis 2003(14): 2259-2264
DOI: 10.1055/s-2003-41444
DOI: 10.1055/s-2003-41444
SPECIALTOPIC
© Georg Thieme Verlag Stuttgart · New York
Straightforward Access to New Cage-Functionalized Sulfur Heterocycles
Further Information
Publication History
Received
6 August 2003
Publication Date:
24 September 2003 (online)


Abstract
Reaction of pentacyclo[5.4.0.02,6.03,10.05,8]undecane-8-thione (7) with diazomethane (9a) and 2-diazopropane (9b) afforded the 1,3,4-thiadiazolines 12a and 12c, which subsequently were used as precursors of reactive thiocarbonyl ylides 13a,b, respectively. Diphenyldiazomethane reacted rapidly with 7 to yield thiirane 14c as the final product. When decomposition of 12a or 12c was carried out in the presence of dipolarophiles, such as TCNE, DMAD or N-methylmaleinimide, new cage-functionalized heterocycles were obtained.
Key words
cage thioketones - diazo compounds - cycloaddition - spiro-heterocycles - thiocarbonyl ylides