ISSN:
0170-2041
Keywords:
ω-Lactims, boryl derivatives of
;
ω-Lactims, condensation of
;
Amidines, N-acyl, borylsulfoboration of
;
ω-Thiolactims, 9-BBN derivatives of
;
ω-Thiolactams
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Diethylborylation and Sulfidation of ω-LactamsSeveral reaction modes of ω-lactams [A (n = 3), B (4), C (5), D (6), E (7), F (11)] with Et3B are observed between 20 and 110°C. The Et2B lactims (1) having various degrees of association [(1a)x; 1b; (1d)2 (X-ray structure); 1e; (1f)4] are formed by elimination of 1 mol of ethane. The condensation products [2b; 2c (X-ray structure)] result by elimination of 1.33 mol of ethane together with the lactim derivatives (3b; 3c). Thermolysis (≥ 125°C) of (1d)2, 1e, and (1f)4 leads to mixtures, in which the compounds 2d, e, f and 3d, e, f, resp., have been identified (NMR, MS). Differences of the thermal behaviour of 1a-f (s-cis/trans conformers, cis/trans lactims, association degree) are discussed. - From 2b, c and Hacac the N-acylamidines (4b, c) are obtained, which react with (9-BBN)2S to yield the monomeric 9-BBN-ω-thiolactims [5b; 5c (X-ray structure)]. The latter react with MeOH to give the ω-thiolactams (6b, c) and 9-MeO-9-BBN, from which the 2:2 MeOH addition compound (7)2 (X-ray structure) is obtained.
Additional Material:
4 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199319930134
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