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
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