Birch Reduction of Aromatic Compounds by A. A. Akhrem PDF

By A. A. Akhrem

ISBN-10: 1475704291

ISBN-13: 9781475704297

ISBN-10: 1475704313

ISBN-13: 9781475704310

Birch aid (see reports [1-5]) is the identify given to the response of unsaturated natural compounds with alkali metals and alcohols in liquid am­ monia. this technique used to be first used for fragrant compounds in 1937 through Wooster [6J, who confirmed that benzene and its derivatives are diminished by means of sodium in liq­ uid ammonia within the presence of an alcohol, whereas this response doesn't happen within the absence of an alcohol. notwithstanding, the final reputation and extensive program of this response used to be completed simply after a sequence of investigations through Birch released from 1944 onwards [7J. because the presence of an alcohol within the response medium isn't really indispen­ sable for pOlycyclic fragrant structures, the current evaluate comprises in basic terms deriv­ atives of the easiest fragrant compounds - benzene and naphthalene. 1 response Mechanism the main possible mechanism of Birch aid, followed by means of the main­ ity of employees during this box [4, eight -12] might be represented through the subsequent phases: 'v\ I NH -'" ,. - i T 1 three +--"'( a) , , ,e (NHa) NH three) + ROH ----+ () ll. . (NHa) A H H four) H H five) ')', ",,\\+ + RO" ~ Q + 110M,,,,,, / (NHa) . (NH:,) Q H H Ii Ij H H H H H+ X/~H M,l

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Download PDF by A. A. Akhrem: Birch Reduction of Aromatic Compounds

Birch aid (see studies [1-5]) is the identify given to the response of unsaturated natural compounds with alkali metals and alcohols in liquid am­ monia. this system used to be first used for fragrant compounds in 1937 via Wooster [6J, who confirmed that benzene and its derivatives are lowered by way of sodium in liq­ uid ammonia within the presence of an alcohol, whereas this response doesn't occur within the absence of an alcohol.

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C:: >-l tTl s: >-l ..... 'Tl t""' 0 ~ <: ..... "l 2171 2161. C19H260 2 No·1 I I ex ,) CHs ! CC I i"y ;olveo" CTI ~ '6z >-3 ~:> Z 'Tl tTl ;;0 c:::: ~>-3 >-3 I-< L" ~ ~ tTl I-< < 00 l IlI . "') I' 2251 2241 223 Li(K). :-JH 3 • NH;j. "C!. Nll a. tert- Ci1"OH, THF (C"H:»~O ~il, iso- C:11I 7 OH. (ClUlU \a. NJ-l;). CI-I 3 0f!. tert- Cll~OH. I"OH, C)I,oH). )20 Li. \H:!. >/"/,, I i Li, NHa. OH, Li, NHs, U. :\11:1' C) I;,C)H. IC)1;;)/). ~/ " ) i. <""'/"" CH" , I , /1----011 / 220, 219 218 f(l I 11 8~1 fliR 187.

I ::<:l 0l:>- eo t-l ..... 0 z ~> z 'Tl ..... I t-l t'"' ..... I <: ..... I I » C1sH2P2 Empirical formula 186 C1sH2P4 I 185 ClsH240a ~8 1 No. I I CHa ,,) 0 ) CHa ~I-OH rlTH ()A/: ,& ~)/i ~ j-(CHz)zCOOH Hi OH CHaO/~ CHa ~ ~ ~/V ~V,) HO ~I-OH CHa Structural formula Starting material I I I C /"')" CH30/~) l/ CHa 0 I CH,)lYY /' CHaj()(Y / I o~~XY / Structural formula Reaction product I i I "0';;\ - (C~H5)P Li, NH a. tert- C4H9OH CZH50H Li, NH 3 , , I I 154 153 - I 156 - I155 Li, NH a, tert-C4 H9OH, (C ZH5 )20 (C ZH5)P ~H50H, Li, NHa, >-0 ...

I t-l t'"' ..... I <: ..... I I » C1sH2P2 Empirical formula 186 C1sH2P4 I 185 ClsH240a ~8 1 No. I I CHa ,,) 0 ) CHa ~I-OH rlTH ()A/: ,& ~)/i ~ j-(CHz)zCOOH Hi OH CHaO/~ CHa ~ ~ ~/V ~V,) HO ~I-OH CHa Structural formula Starting material I I I C /"')" CH30/~) l/ CHa 0 I CH,)lYY /' CHaj()(Y / I o~~XY / Structural formula Reaction product I i I "0';;\ - (C~H5)P Li, NH a. tert- C4H9OH CZH50H Li, NH 3 , , I I 154 153 - I 156 - I155 Li, NH a, tert-C4 H9OH, (C ZH5 )20 (C ZH5)P ~H50H, Li, NHa, >-0 ... ON CH~ Xl") Ha I .

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Birch Reduction of Aromatic Compounds by A. A. Akhrem


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