ISSN:
0009-2940
Keywords:
Dimethylaminobis(trifluoromethyl)borane
;
Nitriles
;
Cyclopropanes
;
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Dimethylaminobis(trifluoromethyl)borane, (CF3)2BNMe2 (A), reacts with Cl(CH2)3CN to yield [Cl(CH2)2CH(CN)](CF3)2B·NHMe2 (1) whereas Br(CH2)3CN and A combine in a 1:2 ratio to form [cyclo-C3H4(CN)](CF3)2B·NHMe2 (2) and Br(CF3)2B·NHMe2. Br(CH2)nCN and A yield [Br(CH2)n-1 CH-(CN)](CF3)2B·NHMe2, n=4 (3), n=5 (4) and n=6 (5). Compound 2 and (NCCH2)CF3)2B·NHMe2 can be alkylated at nitrogen with CH3I/KOH in ether to yield [cyclo-C3H4(CN)]-(CF3)2B·NMe3 (6) and (NCCH2)(CF3)2B·NMe3 (7), respectively. treatment of 1 and 3 with hydroxide in ether gives the respective five- and six-membered heterocycles (CF3)2 (8) and (9). Reduction of the nitrile group with (iBu)2Alh in CH2Cl2 at -50°C followed by hydrolysis furnishes the corresponding aldehydes (OCHCH2) (CF3)2B·NMe3 (10), [cyclo-C3H4(CHO)](CF3)2B·NMe3 (11) and (12). The structure of 2 was determined by an X-ray investigation.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19961291222
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