Fieser And Fieser's Reagents for Organic Synthesis (Volume by Mary Fieser

By Mary Fieser

This ongoing sequence, originated in 1967, has develop into the normal advisor to the education, houses and makes use of of hundreds of thousands of reagents, and extra references to reagents formerly mentioned. It comprises info on structural formulae, molecular weight, actual constants, hottest approach to guidance, and examples of significant makes use of. It additionally includes facts on known reagents from 1966 to 1988.

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Ietir t i BCl. H,)1. orthe (E)-isomerand overallyieldsare in the range8590Vo. Overall yields and isomericpurity are somewhatless in the caseof (Z)isomers. Sequentialcross-couplingcan be used also for synthesisof 1,l-disubstituted (Aldrich). The allylic halogencouplesdirectly alkenesfrom 2,3-dibromopropene with a Grignardreagent;vinylic couplingis slowerand requiresa catalyst(equation I). t h e :ral steps nam (4)' (D cH,:6("' 2#* ,r, R2 c"r:c(lH,*, I F. Montanari. (1957). ,87,1086 2F. ,60,79 (1988).

R nb e * rth one |:tntlomer Bis(acetonitrile)dichloropalladium(II). 1,. Pure(E,E)-, (E,Z)-, (Z,E)-,or (Z,Z)-1,3dienescanbe prepared by this reaction, since the geometry of each partner is retained. The reaction toleratesmany functionalgroups. |,3'Enynes. 2Sincethe conjugatedtriple bond can be reduced to a (Z)-doublebond stereospecifically, the couplingalsoprovidesa route to (z,E)or (z,z)-1,3-dienes. An exampleis thesynthesis of bombykol(l), the sexattractant of the silkworm moth. ryg

Bhupathy,and T. Cohen, Tetrahedron Letters,2E'2203(1987)' N,N'-Bis(salicylidene)ethylenediaminonickel(II), Ni(salen) (1). Supplier: Aldrich. ' Ni(salen). Styrenes oxidationof somealkeneswith NaOCI under phase-transfer Bis(himethylsilyl) setenide ttr'. r. are convertedmainly to epoxidesbut purely ariphaticalkenesare convertedto a mixture of products. ' H. YoonandC. J. Burrows, Am. ,ilO, 40g7(l9gg). )2 Bis(trimethylsilyl)setenide,[(CH3)rSi]rSe (t). )3siosi(cHJJ. )3SiSeLi,which can be regeneratedby a peterson-type elimination (equationI).

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