ISSN:
0170-2041
Keywords:
Ethers, cyclic, cleavage of
;
Sulfoborations
;
Mercaptoalkanols, 9-BBN derivatives of
;
Sulfides, bis(hydroxyalkyl), 9-BBN derivatives of
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Sulfoboration of Cyclic Ethers - A Preparative Route to Mercaptoalkanols and Bis(hydroxyalkyl) SulfidesBis(1,5-cyclooctanediylboryl) sulfide (1) reacts slowly with the cyclic ethers A-D to give the O,S-bis(9-BBN)mercaptoalkanols 2a-d in excellent yields. From oxetane (E) and 1, however, 2e is obtained rapidly, which further reacts with E to yield the bis(9-BBN-oxypropyl) sulfide 3ee. 2a and c react with E to form mixed thioethers 3ae and 3ce, respectively. The methanolysis of 2a-e leads to the O-(9-BBN)mercaptoalkanols 4a-e. The compounds 2 and 3 react with acetylacetone or with 2-aminoethanol to yield the mercaptoalkanols 7a-c, e and the bis(hydroxyalkyl) sulfides 8ae, 8ce and 8ee, resp., in high yields beside the 9-BBN-chelates 5 or 6.
Additional Material:
4 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.1992199201138
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