By Boschke F.L.
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Additional resources for The Chemistry of Organophosphorus Compounds II
Example text
211 R--C--C=P(C~H5)~ + p--CH~C~Hg--SO~NH~ ~] i O C1 212 213 Aus 77 und 209 bildet sich das Acylylid 73 und die Verbindung 210, yon der das Ylid nucleophil das Chloratom unter Bildung des Sahes 217 iibernimmt, das in das chlorierte Acylylid 2"12 und p-Toluolsulfons~ureamid 213 zerf/illt. 51 Umsetzung yon Acyl-alkyliden-triphelxylphosphoranen mit Phenyljodidchlorid Folgendes allgemeines Aufbauverfahren hat sich sehr bewiihrt: aus dem Ylid 90 und einem Thiolester 214 stellt man die Verbindung 73 her 1,51), 16st diese in der ~quivalenten Menge 2n HC1 zum Salz 77 und versetzt die auf 70--80 ~ erwArmte L6sung mit 209.
Analog erhielten Zbiral et al. 236 und 1 Mol S/~urechlorid 705 die Ylide 237 und. die chloride 238: das Allylidenin y-Stellung 10~) aus 2 Mol Phosphonium- 2 ( C ~ H s ) ~ P = C H - - C H = C H 2 -[- R~--COC1 236 105 57 Reaktion yon Phosphinalkylenen @ (CsHs)sP=CH--CH~CH--C--RI + [(C~Hs)sP--CH~--CH=CH~]CI~ ~ 237 0 238 I HX § 'o' ~,~ 9 xo 9 bzw. tt. ~ ~so H H C--R ~ (C~H~)~P=C--C=C~NO 0 ~4~ Die Ylide 237 k6nnen bei der Protonisierung mit H X in zwei verschiedene Phosphoniumsahe 239 (a-Protonisierung) und 240 (y-Protonisierung vgl.
Im Folgenden sollen die Ergebnisse unserer Untersuchungen diskutiert werden at,Sl). Die Tabelle 3 gibt zunXchst einen Uberblick fiber gelungene Allensynthesen. R\ Tabelle 3. Allene ~49 aus der Reaktion yon 2 Mol ~lid R I ~ C ~ P ( C e H s ) ~ 46 m~ einem Mol Sii~re~Morid ~) CHCOCI 139 R Nr. R R1 R 9. Ra l CH~ C~H5 PI H 2 CH~ CoHs H C2H~ Ausbeute an ~ 9 in % d, Th. H~ 3 66 /C~H~ C~C~ 64 37 Umsetzung yon Phosphinalkylenen mit organischen Halogenverbindungen Die Tabelle zeigt, dab es leicht gelingt, Allene darzustellen, wenn im u 46 R aromatisch und R 1 aliphatisch ist.