Reaction of epoxides with boron triisopropoxide. The Meerwein-Ponndorf-Verley type reduction of boron alkoxides. 2 [10]

Bulletin of the Korean Chemical Society

Volumn 23, Issue 10, 2002, Pages 1377-1378

  Cha, Jin Soon ^a   Park, Jae Hyung ^a  

^a Yeungnam University   (South Korea)

Author keywords

Boron triisopropoxide; Epoxide ring opening; MPV type reaction; Reduction

Indexed keywords

BORON DERIVATIVE; BORON TRIISOPROPOXIDE; EPOXIDE; LEWIS ACID; TETRAHYDROFURAN DERIVATIVE; UNCLASSIFIED DRUG;

CHEMICAL REACTION; LETTER; MEERWEIN PONNDORF VERLEY REDUCTION; MOLECULAR DYNAMICS; OUTCOMES RESEARCH; REACTION ANALYSIS;

EID: 0037145569     PISSN: 02532964     EISSN: None     Source Type: Journal    
DOI: 10.5012/bkcs.2002.23.10.1377     Document Type: Letter

References (9)

1. The preceding article: Cha, J. S.; Park, J. H. Bull. Korean Chem. Soc. 2002, 23, 1051.
2. (a) Meerwein, H.; Bock, B.; Kirschnick, B.; Lenz, W.; Migge, A. J. Prakt. Chem. 1936, 147, 211.
3. (b) Woodward, R. B.; Wendler, N. L.; Brutschy, F. J. J. Am. Chem. Soc. 1945, 67, 1425.
4. Brown, H. C.; Yoon, N. M. Chem. Commun. 1968, 1549.
5. Brown, H. C.; Heim, P.; Yoon, N. M. J. Am. Chem. Soc. 1970, 92, 1637.
6. All glassware used was dried thoroughly in an oven, assembled hot, and cooled under a stream of dry nitrogen prior to use. 6. Boron triiopropoxide was prepared by reaction of 10 mL of a 1.0 M solution in THF (10 mmol) and 2.0 g of isopropyl alcohol (33 mmol, 10% excess) at room temperature. See ref 1.
7. All reactions and manipulations of air- and moisture-sensitive materials were carried out using standard techniques for handling air-sensitive materials.9 THF was dried over sodium-benzophenone ketyl and distilled. All liquid materials were transferred by using hypodermic syringes.
8. In cases where a slow stream of dry nitrogen was not employed, the ring-opening reactions of epoxides examined were very sluggish and the conversion yields were much lower.
9. Brown, H. C.; Kramer, G. W.; Levy, A. B.; Midland, M. M. Organic Synthesis Via Boranes; Wiley-Interscience: New York, N. Y., 1975.