Mechanism of the cycloaddition‐elimination reactions of 4‐methyl‐5‐phenylimino‐δ2‐1,2,3,4‐thiatriazoline with alkyl and aryl isothiocyanates
- 1 February 1990
- journal article
- research article
- Published by Wiley in Journal of Heterocyclic Chemistry
- Vol. 27 (2) , 199-204
- https://doi.org/10.1002/jhet.5570270216
Abstract
The formation of thiadiazolidines 3a‐c and dithiazolidines 4a‐c and 5a‐b from the title reactions has been studied in detail under a variety of conditions. On the basis of kinetic measurements, isomerization studies and cross experiments a mechanism is proposed involving path (b) (Scheme 1) as the first step, followed by a series of isomerizations as shown in Scheme 3.Keywords
This publication has 12 references indexed in Scilit:
- A rare case of three rearrangements during the cycloaddition‐elimination reaction of 4‐methyl‐5‐phenylimino‐Δ2‐1,2,3,4‐thiatriazoline with 2‐pyridyl isothiocyanateJournal of Heterocyclic Chemistry, 1988
- Are thiaziridinimines intermediates in the thermolysis of 4-Alkyl-5-arylsulfonylimino-1, 2, 3, 4-thiatriazolines?Bulletin des Sociétés Chimiques Belges, 1988
- Cycloadditions of Ethyl 2-Amino-1-azaazulene-3-carboxylate with Dimethyl AcetylenedicarboxylateHETEROCYCLES, 1987
- Two Fused Five-membered Heterocyclic Rings: (iii) 1,6,6aλ4 -Trithiapentalenes and Related SystemsPublished by Elsevier ,1984
- 4-Alkyl-5-(arylimino)-1,2,3,4-thiatriazolines as masked 1,3-dipolesThe Journal of Organic Chemistry, 1978
- On the alkylation of multisite aromatic heterocycles. Part 2. Formation and thermal decomposition of 4-alkyl-5-alkylimino-1,2,3,4-thiatriazolinesJournal of the Chemical Society, Perkin Transactions 1, 1978
- Synthesis of heterocycles from aryl isothiocyanates and alkyl azidesThe Journal of Organic Chemistry, 1977
- Ringöffnende Cycloadditionen, IV. Reaktion von Iminen der Dithiazol‐ und Isothiazol‐Reihe mit einigen einfachen HeterocumulenenEuropean Journal of Inorganic Chemistry, 1977
- Three‐Component Reactions with Aryl Isothiocyanates. Synthesis of 5‐Arylimino‐1,2,4‐thiadiazolidin‐3‐onesAngewandte Chemie International Edition in English, 1976
- Trapping of thiaziridinimines with heterocumulenesThe Journal of Organic Chemistry, 1975