Intra-annular reactions of the (1,3-xylylene)-18-crown-5 system: synthesis and crystal structure of [2-(bromomagnesio)-1,3-xylylene]-18-crown-5, [2-(bromomercurio)-1,3-xylylene]-18-crown-5 and bis[(1,3-xylylene-18-crown-5)-2-yl]mercury

• Published in: Journal of organometallic chemistry Vol. 463; no. 1; pp. 7 - 21
• Main Authors: Markies, Peter R., Villena, Alan, Akkerman, Otto S., Bickelhaupt, Friedrich, Smeets, Wilberth J.J., Spek, Anthony L.
• Format: Journal Article
• Language: English
• Published: LAUSANNE 1 Elsevier B.V 28.12.1993; Elsevier; Elsevier Science
• Subjects: Chemistry; Chemistry, Inorganic & Nuclear; Chemistry, Organic; Condensed matter: structure, mechanical and thermal properties; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives; Organic chemistry; Organic compounds; Organometalloidal and organometallic compounds; Physical Sciences; Physics; Preparations and properties; Science & Technology; Structure of solids and liquids; crystallography; Structure of specific crystalline solids; X-RAY STRUCTURE; REAGENTS; MACROCYCLIC POLYETHERS; INTRAANNULAR FUNCTIONALIZATION; Molecular structure; Magnesium Bromides; Magnesium Organic compounds; Experimental study; Oxygen heterocycle; X ray diffraction; Macrocycle; Grignard reagent; Bicyclic compound; Mercury Organic compounds; Cyclophane; Magnesium; Nucleophilic substitution; Mercury Bromides; Crystalline structure
• ISSN: 0022-328X; 1872-8561
• DOI: 10.1016/0022-328X(93)83392-9

The Grignard compound [2-(bromomagnesio)-1,3-xylylene]-18-crown-5 ( 4) was prepared from the aryllithium compound (2-lithio-1,3-xylylene)-18-crown-5 The 1 : 1 reaction of 9 with HgBr 2 yielded the corresponding organomercury compound [2-(bromomercurio)-1,3-xylylene]-18-crown-5 ( 10), which The crown ether Grignard 4 was treated with deuterium oxide, chlorotrimethylstannane, iodine and berizophenone to give the products (2- d-1,3-xy