An operationally simple hydroboration-oxidation experiment

Journal Article · Thu Nov 01 04:00:00 EST 1990 · Journal of Chemical Education; (United States)

DOI:https://doi.org/10.1021/ed067p975· OSTI ID:7000087

Kabalka, G W; Wadgaonkar, P P; Chatla, N ^[1]

---

1. Univ. of Tennessee, Knoxville, TN (United States)

The hydroboration-oxidation sequence provides an efficient route to the anti-Markovnikov hydration of alkenes and is one of the most widely used synthetic reactions. The beauty of the hydroboration reaction as a synthetic method stems from the facts that it is broadly applicable, generally quantitative, occurs at ambient temperature, and is highly regio- and stereoselective. The hydroboration-oxidation experiment might thus be expected to enjoy a prominent place in the undergraduate laboratory curriculum. However, it is generally not considered to be suitable for the following reasons: (1) the key reagent, diborane, is somewhat difficult to prepare by traditional methods requiring the use of metal hydrides and strong mineral or Lewis acids (e.g., boron trifluoride etherate); (2) the most commonly used and commercially available hydroborating reagents, borane-tetrahydrofuran (BH[sub 3]-THF) and borane-dimethyl sulfide (BMS), are difficult to manipulate requiring dry and oxygen-free conditions; (3) the standard oxidation procedure requires the use of a dangerous 30% hydrogen peroxide solution. The authors have developed a hydroboration-oxidation experiment that can be readily performed in an undergraduate laboratory in a 4-h laboratory period. The experiment utilizes commercially available, stable, inexpensive, safe, and easily handled reagents and standard laboratory glassware. The reactions involve the use of in situ generated diborane (via reaction of sodium borohydride with iodine) as the hydroborating reagent and sodium perborate as the oxidizing agent.

• DOE Contract Number: FG05-86ER60434
• OSTI ID: 7000087
• Journal Information: Journal of Chemical Education; (United States), Journal Name: Journal of Chemical Education; (United States) Vol. 67:11; ISSN 0021-9584; ISSN JCEDA8
• Country of Publication: United States
• Language: English

Related Subjects

10 SYNTHETIC FUELS
100200 -- Synthetic Fuels-- Production-- (1990-)
99 GENERAL AND MISCELLANEOUS
990000* -- General & Miscellaneous
ALCOHOLS
ALKENES
ANIMALS
BORANES
BORON COMPOUNDS
CHEMICAL REACTION YIELD
CHEMICAL REACTIONS
CYCLOALKENES
EDUCATION
HYDRIDES
HYDROCARBONS
HYDROGEN COMPOUNDS
HYDROXY COMPOUNDS
LABORATORIES
MAMMALS
MAN
ORGANIC COMPOUNDS
OXIDATION
PENTANOLS
PERSONNEL
PRIMATES
PROFESSIONAL PERSONNEL
SCIENTIFIC PERSONNEL
SYNTHESIS
VERTEBRATES
YIELDS