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Novel reactions of sterically protected fused 1,2,3‐selenadiazole. A new aspect of reactivity of organoselenium intermediates
Author(s) -
Ando Wataru,
Kumamoto Yorio,
Tokitoh Norihiro
Publication year - 1988
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.610010603
Subject(s) - chemistry , reactivity (psychology) , nucleophile , steric effects , furan , cycloaddition , derivative (finance) , reagent , diene , selenium , combinatorial chemistry , organic chemistry , medicinal chemistry , photochemistry , computational chemistry , catalysis , medicine , natural rubber , alternative medicine , pathology , financial economics , economics
Light‐ and heat‐induced decompositions and reactions with nucleophiles of 6,6,8,8‐tetramethyl‐2‐selena‐3,4‐diaza‐7‐oxabicyclo[3.3.0]octa‐ 1(5),3‐diene have been studied. In contrast with the conversion to the cyclopentyne derivative ( 9 ), selenium containing intermediates ( 6a, 6b , and 7 ) were efficiently trapped using several reagents to give various kinds of organoselenium compounds. Of particular note is the isolation of a stable selenirane derivative ( 16 ) obtained by the cycloaddition of the photochemically generated selenirene intermediate ( 7 ) with furan. The character and reactivity of the intermediates are also discussed.