MR3-substituted alkynes 2 and 3 (M = Si, Ge, Sn; R = alkyl) show high reactivity in inverse-type Diels-Alder reactions with the re-electron-deficient 1,2,4,5-tetrazine 1 in strict contrast to the corresponding carbon compounds.

Tetrahedron Letters

Volumn 38, Issue 33, 1997, Pages 5791-5794

  Heldmann, Dieter K ^a   Sauer, Jürgen ^a  

^a UNIVERSITY OF REGENSBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOTIN COMPOUND;

ARTICLE; CHEMICAL REACTION KINETICS; DRUG SYNTHESIS; GAS CHROMATOGRAPHY; IN VITRO STUDY; INFRARED SPECTROPHOTOMETRY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS;

BETULACEAE;

EID: 0030818008     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01279-3     Document Type: Article

References (10)

1. Davies, A.G. Tin. In Comprehensive Organometallic Chemistry II; Abel, E. W.; Stone F. G. A.; Wilkinson G., Eds.; Pergamon Press: Oxford, 1995; Vol. 2, pp. 217-303.
2. (a) Seyferth, D.; Envin, A. B. J. Am. Chem. Soc. 1967, 89, 1468-1475.
3. (b) Sakamoto, T.; Funami, N.; Kondo, Y.; Yamanaka, H. Heterocycles 1991, 32, 1387-1390.
4. 2) and concentrated again. The last 50 ml of the solvent were removed under reduced pressure (-40°C, 0.1Torr). Sublimation (bath 10°C, cooling finger -50°C, 0.1 Torr) yielded pure 1 (10.0 - 12.2 g, 21-26%). M.p. 94-95°C.
5. +].
6. An 8-10 fold excess of the volatile dienophile was used in order to accelerate the reaction.
7. -1). Deviations for at least four runs were always less than 4%.
8. Sauer, J. 1,2,4,5-Tetrazines. In Comprehensive Heterocyclic Chemistry II; Katritzky A. R.; Rees, C. W., Eds.; Pergamon Press: Oxford, 1997; Vol. 6, pp. 901-957.
9. +].
10. +-H].