ISSN:
0009-2940
Keywords:
1,2,5-Azasilaboroles, organo-2,5-dihydro-
;
Dihydroxyalkanes(arenes)
;
1,6-Dioxa-2-sila-5-bora-3-cycloalkenes
;
Regio- and stereoisomers
;
Metathesis, BO
;
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Organosubstituted 1,6-Dioxa-2-sila-5-bora-3-cycloalkenes - Preparation and Characterisation1)The cis-alkenes ROSi(CH3)2C(R) = C(C2H5)B(C2H5)OR (R = CH3: 11; C2H5: 12; C6H5: 13) are prepared from CH3NSI[CH3)2C(R)=C(C2H5)BC2H5 [R = CH3: A; R = C(CH3) = CH2: B] with the monohydroxy compounds ROH (R = CH3, C2H5, C6H5). A or B react with aliphatic dihydroxy compounds HO—R′—OH [R′ = —CH2CH2—: 1; —CH(CH3)CH2—: 2; —CH(CH3)—CH(CH3)—: 3; —C(CH3)2C(CH3)2—: 4; —(CH2)3: 5; —(CH2)4—: 6] to give 8-, 9-, and 10-membered ring compounds OSi(CH3)2C(R) = C(C2H5)OR′ [15a,b, 16/16′, meso/rac-17a, D-17a,b, 18, 19, (20)n]. A is initially cleaved at the SiN bond with formation of 14 Compound 15a crystallises as the 16-membered (15a)2 [X-ray structure analysis). The aromatic dihydroxy compounds catechol (7), resorcinol (8), 2,3-dihydroxynaphthalene (9), 1, 8-dihydroxynaphthalene (10) react with A to form 21 to 24, but mainly by protolytic BCvinyl fission to give the 2,5-dihydro-1,2,3-dioxaboroles (e.g. 7f1, 9f1, 10f1) and the acyclic boron-free compounds 7f′3, 9f3, 10f3. The MS and NMR (1H, 11B, 13C, 29Si) data of the new compounds are discussed.
Additional Material:
2 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19901230514
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