Stereochemistry of heterocycles

Bogatskii, A. V.; Samitov, Yu. Yu.; Gren, A. I.; Соболева, С. Г.

doi:10.1007/bf00475706

Cited by 2 publications

(2 citation statements)

References 10 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Study of the transformation of two samples of the initial 1,3-dioxane with different configurational composition [23,25] showed that the cis isomer reacted more quickly than the trans isomer in both cases; here the borylation is strictly stereospecific; the cis isomer is only transformed into the cis form of 1,3,2-dioxaborinane while the trans form of the cyclic boric ester is formed exclusively from the trans isomer. (The stereochemistry of 2-isobutyl-5-isopropyl-4-methyl-1,3,2-dioxaborinane was studied in detail in [26].)…”

Section: Borylation Of 13-dioxanesmentioning

confidence: 98%

See 1 more Smart Citation

Borylation of saturated heterocycles with several heteroatoms. (Review)

Кузнецов

2006

Chem Heterocycl Compd

View full text Add to dashboard Cite

New examples of the borylation of a series of five-and six-membered saturated 1,3-and 1,3,2-heterocycles with the formation of cyclic boric esters are described. The probable mechanism of the reaction is discussed.A promising trend in the synthesis of cyclic boric esters, which are important reagents in organic chemistry, is the reaction of alicyclic boron substrates with saturated 1,3-or 1,3,2-heterocycles.XY 2 Z = O, NR; X = CR 1 R 2 , SiR 1 R 2 , S=O, GePh 2 , As(O)Ph; Y = OR, Cl; n = 0, 1 + Z Z + Early papers on this subject, which appeared in the second half of the twentieth century, were fragmentary in nature and were devoted to the borylation of 1,3-dithia-3-silacyclopentanes [1, 2], bis(1,3-diphenylimidazolidin-2-ylidene) [3], substituted 1,3-dioxanes [4][5][6][7], and six-membered silicon-and nitrogencontaining heterocycles [8]. In the last decade, however, it has been possible to discover interesting new examples of such reactions, to investigate their occurrence and stereochemistry in detail, and to obtain information about their probable mechanism.

show abstract

Section: Borylation Of 13-dioxanesmentioning

confidence: 98%

“…However, the position changes in the case of 4,5-dialkyl-1,3-dioxanes, the stereochemistry of which was investigated in [23]; according to GLC, cis-4-methyl-5-isopropyl-1,3-dioxane reacts with the acyclic boric substrate more rapidly that the trans form (Table 3) [24]. [24].…”

Section: Borylation Of 13-dioxanesmentioning

confidence: 99%