SYNTHESIS AND REACTIVITY OF SOME 4-BROMO- 2H-CHROMENES AND 2H-THIOCHROMENES

• Published in: Tetrahedron Vol. 50; no. 8; pp. 2507 - 2522
• Main Authors: GABBUTT, CD, HARTLEY, DJ, HEPWORTH, JD, HERON, BM, KANJIA, M, RAHMAN, MM
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier 21.02.1994
• Subjects: Chemistry; Chemistry, Organic; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives; Organic chemistry; Physical Sciences; Preparations and properties; Science & Technology; ORGANOPHOSPHORUS COMPOUNDS; DERIVATIVES; ACID; Sulfur heterocycle; Ketoether; Electrophilic substitution; Bromination; Bicyclic compound; Aromatic compound; Haloether; Oxygen heterocycle; Chemical reactivity; Ketosulfide; Halogenides sulfides

A facile synthesis of 4-bromo- 2H-chromenes and 2H-thiochromenes and of 1-bromo-3,4-dihydronaphthalene from the corresponding ketones and PBr3 is described. In some instances, significant quantities of the phosphonic acids (3) are isolated. Conversion of the bromo compounds to the lithio derivatives...