Sulfur ylides generated from the reaction of adamantylidene and phenylcarbene with sulfur substrates

Reaction of adamantylidene and phenylcarbene with ethylthiol, ethylene dithiol, allylethylsulfide, allylphenylsulfide, and trimethylenesulfide involves the formation of a sulfur ylide intermediate, followed by H-migration, 2,3-sigmatropic shift, or ring opening to give sulfides. The sulfur ylide formed in the reaction of phenylcarbene with trimethylenesulfide is directly observed by laser flash photolytic techniques. (C) 2003 Elsevier Ltd. All rights reserved.PT: J; CR: ADMASU A, 1997, J PHYS CHEM A, V101, P3832 ADMASU A, 1997, J PHYS ORG CHEM, V10, P207 ANDO W, 1977, ACCOUNTS CHEM RES, V10, P179 ANDO W, 1978, CHEM DIAZONIUM DIAZO, CH9 DOYLE MP, 1986, CHEM REV, V86, P919 DOYLE MP, 1998, CHEM REV, V98, P911 ISAEV SD, 1973, ZH ORG KHIM+, V9, P724 PADWA A, 1991, CHEM REV, V91, P263 PADWA A, 1996, CHEM REV, V96, P223 ROMASHIN YN, 2001, TETRAHEDRON LETT, V42, P207 SMITH RAG, 1975, J CHEM SOC P2, P686 TROST BM, 1975, SULPHUR YLIDES; NR: 12; TC: 2; J9: TETRAHEDRON LETT; PG: 3; GA: 709GZSource type: Electronic(1