A novel transformation of 1-exo-substituted 2a-aroyl-1,2,2a,8b-tetrahydro-3H-benzo[b]cyclobuta[d]pyran-3-ones with sulfoxonium ylide to highly strained 2a-(1-arylethenyl)-1,2,2a,7b-tetrahydrocyclobuta[b]benzofurans

Tetrahedron Letters

Volumn 49, Issue 10, 2008, Pages 1627-1630

  Yadav, Navnath Dnyanoba ^a   Yamashita, Masayuki ^a   Nagahama, Masaki ^a   Inaba, Tomoki ^a   Sawaki, Takeshi ^a   Kawasaki, Ikuo ^a,b   Kurume, Ai ^a   Ohta, Shunsaku ^a  

^a KYOTO PHARMACEUTICAL UNIVERSITY   (Japan)

^b MUKOGAWA WOMEN'S UNIVERSITY   (Japan)

Author keywords

3H Benzo b cyclobuta d pyran; Cyclobuta b benzofuran; Skelton transformation; Sulfur ylide; Tetrahydrodibenzofuran

Indexed keywords

2A (1 ARYLETHENYL) 1,2,2A,7B TETRAHYDROCYCLOBUTA[B]BENZOFURAN DERIVATIVE; 2A AROYL 1,2,2A,8B TETRAHYDRO 3H BENZO[B]CYCLOBUTA[D]PYRAN 3 ONE DERIVATIVE; 3 AROYL 1,2,4A,9B TETRAHYDRODIBENZOFURAN 4 OLS; BENZOFURAN DERIVATIVE; DIMETHYL SULFOXIDE; PYRAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 38949169514     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.01.032     Document Type: Article

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10. 20O: C, 88.85; H, 6.21. Found: C, 88.72; H, 6.26.
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12. The selectivity of 2 and 3 at 0 °C was moderate, but the reaction time was long. Though its selectivity at 80 °C was low, the reaction time was short. Therefore, this reaction condition was chosen in consideration for product ratio and time.
13. The reason why this reaction occur in only 1-exo-1 of which substituent groups at the 2a position is the aroyl group is not clear. The theoretical calculation will disclose this result.