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Volumn , Issue 11, 2006, Pages 1750-1752

Carbonyl propargylation and allenylation with 2-propynyl mesylates, tin(IV) iodide, and tetrabutylammonium iodide controlled by either a steric effect or coordination effect

Author keywords

Allenylation; Nucleophilic addition; Propargylation; Tetrabutylammonium iodide; Tin(IV) iodide

Indexed keywords

1 METHYL 2 PROPYNYL MESYLATE; 2 BUTYNYL MESYLATE; 2 PROPYNYL MESYLATE DERIVATIVE; 3 TRIMETHYLSILYL 2 PROPYNYL MESYLATE; ALDEHYDE DERIVATIVE; CARBONYL DERIVATIVE; DICHLOROMETHANE; IODINE DERIVATIVE; MESYLIC ACID DERIVATIVE; SILANE; STANNOUS IODIDE; TETRABUTYLAMMONIUM; UNCLASSIFIED DRUG;

EID: 33746295042     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-944222     Document Type: Article
Times cited : (5)

References (33)
  • 4
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  • 5
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    • (1995) Modern Acetylene Chemistry
  • 24
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    • For the preparation of allenyltin and propargyltin compounds, see: (a) Guillemin, J.-C.; Malagu, K. Organometallics 1999, 18, 5259.
    • (1999) Organometallics , vol.18 , pp. 5259
    • Guillemin, J.-C.1    Malagu, K.2
  • 31
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    • note
    • 2, s).
  • 32
    • 0000296781 scopus 로고
    • (a) Since 1b caused no carbonyl propargylation, 3- methylpropargyltriiodotin would scarcely isomerize to 1-methylallenyltriiodotin on account of the steric hindrance of the methyl group. Thus, the bulkier trimethylsilyl group should give an unusual effect for the isomerization of A to C. It is presumed that the formation of a higher coordinated silicon intermediate causes regioselective ring-opening reactions of α-silylepoxides at the α-carbon near to the silyl group: Eisch, J. J.; Galle, J. E. J. Org. Chem. 1976, 41, 2615.
    • (1976) J. Org. Chem. , vol.41 , pp. 2615
    • Eisch, J.J.1    Galle, J.E.2
  • 33
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    • (b) Soderquist, J. A.; Santiago, B. Tetrahedron Lett. 1989, 30, 5693. Following the ring-opening reactions of α-silylepoxides, we propose stannylsilicate B as a plausible intermediate for the isomerization of A to C.
    • (1989) Tetrahedron Lett. , vol.30 , pp. 5693
    • Soderquist, J.A.1    Santiago, B.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.