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Cycloadditionen von 2H ‐Benzo[ b ]thiet und Verbindungen mit kumulierten Doppelbindungen
Author(s) -
Gröschl Dieter,
Niedermann HansPeter,
Meier Herbert
Publication year - 1994
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.19941270525
Subject(s) - chemistry , allene , cycloaddition , double bond , ketene , adduct , imine , stereochemistry , ring (chemistry) , yield (engineering) , medicinal chemistry , polymer chemistry , organic chemistry , catalysis , materials science , metallurgy
Cycloaddition Reactions of 2H ‐Benzo[b]thiete and Compounds with Cumulated Double Bonds o ‐Thiobenzoquinone methide (2) , generated by thermal ring opening of 2H‐benzo[ b ]thiete ( 1 ), reacts with allene 3 , ketene imine 7 , the carbodiimides 9a‐c , and the N ‐sulfinylamines 11a‐c in highly specific [8π + 2π] cycloaddition processes to form novel types of heterocyclic systems 4, 8, 10a‐c , and 12a‐c with exocyclic double bonds. The 1:1 adduct 4 can add a further molecule of allene to yield the spiro compounds 5 and 6 .