6533b873fe1ef96bd12d5fb7

RESEARCH PRODUCT

Cycloadditionen von 2H ‐Benzo[ b ]thiet und Verbindungen mit kumulierten Doppelbindungen

Herbert MeierHans‐peter NiedermannDieter Gröschl

subject

Inorganic Chemistrychemistry.chemical_classificationchemistry.chemical_compoundDouble bondchemistryBicyclic moleculeStereochemistryAlleneImineKeteneRegioselectivityRing (chemistry)Cycloaddition

description

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.

https://doi.org/10.1002/cber.19941270525