New Addition Reactions of Organometal Compounds with 4,4‐Dimethyl‐1,3‐thiazole‐5(4 H )‐thiones | Zendy

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New Addition Reactions of Organometal Compounds with 4,4‐Dimethyl‐1,3‐thiazole‐5(4 H )‐thiones

Author(s) -

Shi Junxing,

Heimgartner Heinz

Publication year - 1996

Publication title -

helvetica chimica acta

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.74

H-Index - 82

eISSN - 1522-2675

pISSN - 0018-019X

DOI - 10.1002/hlca.19960790206

Subject(s) - chemistry , thiazole , reagent , alkyl , grignard reagent , medicinal chemistry , organic chemistry , combinatorial chemistry

Addition reactions of organometallic reagents with 4,4‐disubstituted 1,3‐thiazole‐5(4 H )‐thiones were studied. Whereas the reactions with alkyllithium and alkyl Grignard reagents occurred in the thiophilic manner, the carbophilic addition was observed with allyllithium and allyl Grignard reagents. A radical reaction mechanism is proposed for rationalizing these observations ( Scheme 5 ). A radical cyclization of the prepared 5‐allyl‐4,5‐dihydro‐1,3‐thiazole‐5‐thiol derivatives yielded 1,6‐dithia‐3‐azaspiro[4.4]non‐2‐enes ( Table 4 ).

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