๐”– Bobbio Scriptorium
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Dimethylboron bromide and diphenylboron bromide. Acetal and ketal cleavage. Cleavage of MEM, MOM, and MTM ethers.

โœ Scribed by Yvan Quindon; Howard E. Morton; Christiane Yoakim

Book ID
104221559
Publisher
Elsevier Science
Year
1983
Tongue
French
Weight
256 KB
Volume
24
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

Reaction of menthol-MEM ether with Me2BBr gave, after quenching with sat. aq. sodium bicarbonate in the absence of tetrahydrofuran (see Experimental), a mixture of menthol and formaldehyde-dimenthol ketal in 61 and 15% yield, respectively.

We have previously cleaved this acetonide using HCl(5N)-EtOH at 60ยฐC for 1 h in yields ranging from 50 to 70%.

๐Ÿ“œ SIMILAR VOLUMES

Ring cleavage of THP and THF ethers usin
Ring cleavage of THP and THF ethers using dimethylboron bromide
โœ Yvan Guindon; Michael A Bernstein; Paul C Anderson ๐Ÿ“‚ Article ๐Ÿ“… 1987 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 256 KB

The reactlon of dlmethylboron bromlde with THP and THF ethers was studled. Under condltlons of klnetlc control. these reacttons proceed by selective cleavage of the ring carbon-oxygen bond to glve acyclIc a-bromo ethers. Treatment of these lntermedlates with a variety of nucleophiles gives ring-open