Novel, five-membered cyclic betaines from the reaction of an ethynyl- hydrazine with aryl isothiocyanates

Tetrahedron Letters

Volumn 39, Issue 37, 1998, Pages 6671-6674

  Himbert, Gerhard ^a   Gerulat, Oliver ^a   Matheis, Steffen ^a   Bergsträßer, Uwe ^a  

^a Rheinland Pfälzische Technische Universität Kaiserslautern Landau   (Germany)

Author keywords

(1 alkynyl)hydrazine; Betaines; Cycloaddition; Electrocyclic ring opening

Indexed keywords

BETAINE; HYDRAZINE DERIVATIVE; ISOTHIOCYANIC ACID DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; SPECTROSCOPY;

EID: 0032505211     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01356-2     Document Type: Article

References (17)

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3. b) Himbert, G.; 1-Diorganoamino-1-alkine, Umwandlungen. In Methoden der Organischen Chemie; Thieme; Stuttgart, 1993; Vol. E 15, pp. 3404-3443.
4. 2. Gerulat, O.; Himbert, G.; Bergsträßer, U. Synlett 1995, 835-836.
5. 3. Products 7 were isolated as yellow or orange crystalline compounds in about 50% yield: mp: (7a) 137 - 8°C; (7b) 108 - 9°C; (7c) 126 - 7°C; (7d) 113 - 6°C.
6. 13C-values) and their comparison with those of the isocyanate adducts 3 point out the existence of betaines, but at the very least, they do not reveal the positions of the thioxo-and of the arylimino group.
7. -3. Further details of the crystal structure of compound 7b can be obtained from the Cambridge Crystallographic Data centre, 12 Union Road, Cambridge CB2 1EZ (UK) on quoting the full journal citation.
8. 6. a) Sheldrick, G. M. SHELXS-86, Programm for the Solution of Crystal Structures. 1986, University of Göttingen, Germany
9. b) Sheldrick, G. M. SHELXL-93, Programm for the Refinement of Crystal Structures. 1993, University of Göttingen, Germany
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11. 7. Zvilichovsky, G.; Gurvich, V.; Cohen, S. J Chem. Res. (S) 1994, 335; J. Chem. Res. (M) 1994, 1801-1812.
12. 9] and/or with the C/N bond [10] of isothiocyanates.
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14. 10. Dondoni, A.; Kniezo, L.; Medici, A. J. Org. Chem. 1982, 47, 3994-3997; Kniezo, L.; Kristian, P.; Dondoni, A.; Pedrini; P.; Andreetti, G. D.; Ugozzoli, F. J. Chem. Res. (S) 1986, 40-41; J. Chem. Res. (M) 1986, 537-578.
15. 10. Dondoni, A.; Kniezo, L.; Medici, A. J. Org. Chem. 1982, 47, 3994-3997; Kniezo, L.; Kristian, P.; Dondoni, A.; Pedrini; P.; Andreetti, G. D.; Ugozzoli, F. J. Chem. Res. (S) 1986, 40-41; J. Chem. Res. (M) 1986, 537-578.
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17. 11. We isolated our desilylated products (see 10) by column chromatography in about 80% yield as yellow to orange compounds: mp: (10a) 123 - 4°C; (10b) 102 - 103°C; (10c) 109 -111°C; (10d) 109 -110°C.