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Volumn 71, Issue 9, 2006, Pages 3630-3633

Radical-mediated 5-exo-trig cyclizations of 3-silylhepta-1,6-dienes

Author keywords

[No Author keywords available]

Indexed keywords

SILANES; STABILIZATION; SULFUR COMPOUNDS;

EID: 33646265303     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo060024+     Document Type: Article
Times cited : (31)

References (39)
  • 10
    • 33646234184 scopus 로고    scopus 로고
    • note
    • For the synthesis of precursors 3a-d, see the Supporting Information.
  • 11
    • 0043074883 scopus 로고    scopus 로고
    • 2Ph and SePh was assigned on the basis of related studies; see: (a) Chabaud, L.; Landais, Y. Tetrahedron Lett. 2003, 44, 6995-6998.
    • (2003) Tetrahedron Lett. , vol.44 , pp. 6995-6998
    • Chabaud, L.1    Landais, Y.2
  • 24
    • 33646254087 scopus 로고    scopus 로고
    • note
    • As mentioned by one referee, fragmentation of the tosyl group is probably more affected than the 5-exo-trig cyclization by lowering the temperature due to entropy effects.
  • 27
    • 33646236511 scopus 로고    scopus 로고
    • note
    • 2SePh, at temperatures ranging from -70 °C to rt, led to no reaction.
  • 29
    • 33646250392 scopus 로고    scopus 로고
    • note
    • The exact mechanism of the elimination process 8a → 8b, under such conditions, is unknown, and one cannot exclude the β-elimination of the silicon group through an ionic pathway.
  • 30
    • 0002325661 scopus 로고    scopus 로고
    • 3 group. This probably results from a protonation of the allylsilane moiety under the reaction conditions, followed by a rapid electrophilic 5-exo cycloetherification. For a similar process, see: Akiyama, T.; Ishida, Y. Synlett 1998, 1150-1152. (Equation Presented)
    • (1998) Synlett , pp. 1150-1152
    • Akiyama, T.1    Ishida, Y.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.