Unusual ring-expansion reaction of polyfluorinated norbornenoxetanes

Synthesis

Volumn , Issue 9, 2007, Pages 1349-1354

  Petrov, Viacheslav ^a   Marshall, Will ^a  

^a DUPONT COMPANY   (United States)

Author keywords

4 halomethyl 4 trifluoromethyl 3 oxatricyclo 4.2.1.02,5 non 7 enes; LDA; Methyllithium; n butyllithium; Ring expansion reaction

Indexed keywords

METHYLLITHIUM; POLYFLUORINATED NORBORNENOXETANES; RING EXPANSION REACTION;

ALCOHOLS; CYCLIZATION; EXPANSION; LOW TEMPERATURE EFFECTS; QUENCHING; REACTION KINETICS;

PARAFFINS;

2,3 DIHYDRO 4 TRIFLUOROMETHYL 5 X FURAN DERIVATIVE; 2,3 DIHYDRO 4 TRIFLUOROMETHYLFURAN; 4 HALOMETHYL 4' TRIFLUOROMETHYL 3 OXATRICYCLO[4.2.1.0 2,5]NON 7 ENES; ALKYL LITHIUM; FURAN DERIVATIVE; LITHIUM 3 (1,1 DIHALO 3,3,3 TRIFLUOROPROP 1 EN 2 YL)BICYCLO[2.2.1]HEPT 5 EN 2 ALKOXIDE DERIVATIVE; LITHIUM DERIVATIVE; LITHIUM DIISOPROPYLAMIDE; NORBORNENE DERIVATIVE; NORBORNENOXETANE DERIVATIVE; OXETANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; FLUORINATION; LOW TEMPERATURE; SYNTHESIS;

EID: 34249029650     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-965999     Document Type: Article

References (8)

1. DuPont publication no. 8777.
2. Petrov, V. A.; Vasil'ev, N. V. Curr. Org. Synth. 2006, 3, 215.
3. Petrov, V. A.; Davidson, F.; Smart, B. E. J. Fluorine Chem. 2004, 125, 1543.
4. Petrov, V. A. Mendeleev Commun. 2006, 155.
5. Ichikawa, J.; Wada, Y.; Okauchi, T.; Minami, T. Chem. Commun. 1997, 1537.
6. Ichikawa, J.; Wada, Y.; Fujiwara, M.; Sakoda, K. Synthesis 2002, 1917.
7. Ichikawa, J.; Nadano, R.; Mori, T.; Wada, Y.; Holle, S.; Fürstner, A. Org. Synth. 2006, 83, 111.
8. Crystallographic data (excluding structure factors) for 11a are deposited with the Cambridge Crystallographic Data Centre as CCDC 635359. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44(1223)336033 or e-mail: deposit@ccdc.cam.ac.uk].