Rxns 227 Fall13 Rxns 23-26

Rxns 227 Fall13 Rxns 23-26 - Reaction 23 Reduction of...

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Unformatted text preview: Reaction 23. Reduction of alkynes with Lithium or Sodium in Ammonia. McMurr 9.5 - 324 Rea ents and conditions Lithium or sodium methat in liquid ammonia are used to obtain the trans product Mechanistic details Li or No reduction involves an electron-transfer process which goes through an intermediate vinylic carbonion Examples: , .o— \ Cl—l ea c. CH —-—> a <— ’ ¢ 3 5 MH3( L539 42 C H/ \CH3 3‘: '..f Hall-lg 5 .— H kl we :___ __—;. /\/\ fizzle Li _ UWWCWW $7?er = L) NRHCQ é ( N Liz; I) on 6—H E /\ Lt) \Cfl C! 2' 3 Mcmurfi‘ Q ~——-—-——>- / ’— \ 4,18% v CHBCRZ D P. J. Santandcr .i’li-‘all l3 Reaction 24. Oxidafive cleavage of alkynes. Mc.Mur‘r 6.7 188 Rea - em‘s and conditions Examples: A 0 O H H x l /\ 93 o\ C /\/\/\/\/Y° at UL ‘ \——:-—_—. —/ 2.) H10 1; A Ln? 2" O V‘ ‘ I / Q02 H. ‘2. \ 2") H+, HLO O c:—..=.c. TC 5 C43le 0 (roan W ‘HL ‘ 3 3’ ~—————-——-——> “OOC~(CR7,) CH C-HgCALCoolrg 13 03 SW; ‘3 C" R ———'—‘—~> cooH Q0 q <—/ 2) H20 0 Z. 5132, é/ K‘W‘f m “9% \ / "———-37 OH Cfll , 333 5 /\[/\ HBO? CH (CH CooH 1x 03 3 a" Care? 4: CR1) (CR2) E C (CH-AZCEE Hog CHLC’H‘LCDOH 332’ P. J. Santander /I'-‘21[l '13 Reaction 25. Alkylafion of acetylide anion. Mc.Mur'r' 9.7 325- Reaen‘rs and conditions Mechanisfic defails KNHZ or muwfll DEA 3:42. Suloskfwkm GL3 a, 10059, (‘m HHS orTHF) madacmifiwu ( More Km Chad?!” H 3 , Privmoxa ekecl‘ropl’tiles ! Examples: ') “QM”;— n 1’ SW‘CHN 40: ‘ Q'C’EGH ———-——-> Cat-— 25 Agr 3r EV 2- \/\\ ____>N°"°“‘ _,__7 \/\%\\/\ \\ N“3( 3 >~~ w 5—}, gruim'fizl " 1> >—\ @r Klan/L ‘ 0.,” HL E B momma 6 M HZ @Sv hm L) A: z> </__\ CH2: NH M; g 1) CHBC’HLEW (’3 ® ‘ gr- CHBCHZCHLCRLQEC-C'H Gal-’0 [Cfigmzcflzmlc‘éw * O“??me 857‘ P. J. Sanlandcr f1"2lll 'l3 shah: {laser 30! Reaction 26. Allylic brominafion. Mc.Murr 10.3 - 349 Mechanistic details radical) reackm regencmce Slu‘rucl’vres oi: 'HAa Emmi-5A FACLJCAI Mu Lee. gougCAer-eoK JOE. Preéuid‘ Posgfb‘a ProcLJQ . Examples: N CHZZCH CHzCHZCH'S L A \ QRL: CR CH'LCHLCRLCHB act 3 K 91- CH : CH data-12m?) its? 4 gr 6r M S / “CHM”; 2. m —-—%—-—> L~_/ 3m- Br “00°C, ._ 3 A 4. Q1 .___.__>. CACHLC. _. CA1 WILL???" 5 fl / 1933’> AK “/ Cw 1- k Em) 6r ér Law! P. J. Santander /'1-‘a|l 13 ...
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