Unexpected switching between addition and substitution in the rhodium- catalysed reaction between tin hydrides and propargyl ethers

Synlett

Volumn , Issue 8, 1999, Pages 1259-1260

  Mitchell, Terence N ^a   Moschref, Said Nadjib ^a  

^a TU DORTMUND UNIVERSITY   (Germany)

Author keywords

Addition; Regiochemistry; Rhodium catalysis; Substitution; Tin hydride

Indexed keywords

ETHER DERIVATIVE; HYDROGEN; ORGANOTIN COMPOUND; RHODIUM;

ARTICLE; CATALYSIS; NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0032769781     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2794     Document Type: Article

References (9)

1. Zhang, H. X.; F. Guibé, F.; Balavoinc, G. J. Org. Chem. 1990, 55, 1857.
2. Kikukawa, K.; Umekawa, H.; Wada, F.; Matsuda, T. Chem. Lett. 1988, 881.
3. Miyake, H.; Yamamura, K. Chem. Lett. 1989, 981.
4. Mitchell, T. N.; Gießelmann, F.; Kwetkat, K. J. Organometal. Chem. 1995, 492, 191.
5. Takeuchi, R.; Nitta, S.; Watanabe, D. J. Org. Chem. 1995, 60, 3045.
6. 3P (21 mg, 0.04 mmol) are placed in a round-bottomed flask under argon; absolute acetone (12 mL) is added and the mixture stirred for 5 min. The alkyne (8 mmol) and the tin hydride (12 mmol) are now added and the reaction mixture stirred for 16 h at 50 °C. Volatiles are removed and the resulting oil fractionated under reduced pressure.
7. 5H).
8. 7H).
9. Moschref, S.-N. Dissertation, Dortmund 1999.