A general synthesis of β-silylallenes from allylsilanes

Tetrahedron Letters

Volumn 38, Issue 19, 1997, Pages 3395-3398

  Lahrech, Mokhtar ^a   Hacini, Salih ^a   Parrain, Jean Luc ^b   Santelli, Maurice ^b  

^a UNIVERSITY OF ORAN   (Algeria)

^b AIX MARSEILLE UNIVERSITY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALLENE DERIVATIVE; ORGANOSILICON DERIVATIVE;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; IN VITRO STUDY; INFRARED SPECTROPHOTOMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS;

EID: 0030915997     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00628-X     Document Type: Article

References (21)

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15. PM3 semi-empirical calculation method applied to 1h reveals a high HOMO level compared to HOMO level of allyltrimethylsilane. In spite of this, for the HOMO, the sp2 carbons exhibit very weak orbital coefficients leading to a bad overlapping that can explained the unreactivity of 1h toward dibromocarbene.
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18. 13C NMR, MS).
19. Preparation of 1,5-bis(trimethylsilyl)penta-2,3-diene 3e: Bromoform (17 mmol) was added, at 0° C, to 1,4-bis(trimetylsilyl)but-2-ene (10mmol) and potassium tert-butoxide (17mmol) in suspension in pentane (10mL). The mixture was stirred for 1h., warmed to room temperature for 10 mn, extracted with ether (3×10 mL) and the combined organic layers dried. The solvents were removed to give 2e. Chromatography on silica gel eluting with light petroleum ether gave a colorless oil.
20. -1.
21. Wadman, S.; Whitby, R.; Yeates, C.; Kocienski, P.; Cooper, K. J. Chem. Soc., Chem. Comm. 1987, 214-243