650-06-6Relevant articles and documents
Components of the sex pheromone of Chilo supressalis: Efficient syntheses of (Z)-11-hexadecenal and (Z)-13-octadecenal
Gil,Lazaro,Mestres,Millan,Parra
, p. 351 - 361 (1995)
(Z)-11-Hexedecenal 1a and (Z)-13-octadecenenal 2a, components of the sex attractant pheromone of Chilo supressalis, have been synthesized as their ethylene acetals 1b and 2b from cyclododecanone 3, through intermediacy of the C12 ω functionalized acetals 8 and 12.
A simple and practical synthetic protocol for acetalisation, thioacetalisation and transthioacetalisation of carbonyl compounds under solvent-free conditions
Khan, Abu T.,Mondal, Ejabul,Ghosh, Subrata,Islam, Samimul
, p. 2002 - 2009 (2007/10/03)
A wide variety of carbonyl compounds can be converted smoothly to the corresponding acetals on treatment with alcohols or diols and triethyl orthoformate in the presence of a catalytic amount of (bromodimethyl)sulfonium bromide at room temperature. Similarly, various carbonyl compounds can be transformed into the corresponding dithioacetals on reaction with thiol or dithiols at room temperature by employing the same catalyst without any solvent. Moreover, O,O-acetals can also be converted into the corresponding dithioacetals under identical conditions. Some of the major advantages are mild reaction conditions, a high degree of efficiency, compatibilty with other protecting groups and the lack of solvents, particularly for thioacetalisation. In addition, no brominations occur at the double bond or α to the keto position or even in the aromatic ring under these experimental conditions. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
Triethylborane-Induced Hydrodehalogenation of Organic Halides by Tin Hydrides
Miura, Katsukiyo,Ichinose, Yoshifumi,Nozaki, Kyoko,Fugami, Keigo,Oshima, Koichiro,Utimoto, Kiitiro
, p. 143 - 147 (2007/10/02)
The reduction of organic halides with tributyltin hydride in the presence of a catalytic amount of triethylborane has been studied. (1) Alkyl iodides and alkyl bromides reacted easily with tin hydride at -78 deg C to give the corresponding hydrocarbons, while alkyl chlorides were sluggish to react and recovered unchanged. (2) The reduction of alkenyl halides such as 1-deuterio-1-iodo-1-dodecene and 1-iodo-1-triethylsilyl-1-dodecene proceeded nonstereospecifically. (3) The reduction of aryl halides with n-Bu3SnH-Et3B system was not so effective as the reduction of alkyl halides and alkenyl halides.Whereas aryl iodides were reduced at room temperature with n-Bu3SnH, aryl bromides hardly reacted with n-Bu3SnH even at 80 deg C.
