Solvomercuration / Demercuration Reactions in Organic by Professor Richard C. Larock (auth.)

By Professor Richard C. Larock (auth.)

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2. ) AcOHgCH2CHOHCH2NHCOICHOH),CH20H (wrong regloisomer HOCH 2CHIHgOAc) NHC0 2 ICH 2 )2CHIC H3)2 HO CH20H ACOH9CH2CHOHCH20~ HO AcOHgCH2CHOHCH20CH2CHCH2 CH 3, lH3 C NaBH,/ NaOH HO 94 74 100 99 162 94 OH 98 94 Ret. j:>. ) HOCH2CHIH90ACICH2NHCO~N ? AcOHgCH2COCsHs 0, 0, CHJCHOHCHOH-Q-O 94 98 102-104 105 104,105 98 255e 100 13,101 XH9CH2CHOHCH2-Q-0 X = Cl, Br, I H2C=CI02CCIICICHJiJ 1551 Ref. 2. (continued) ...... o· :::s ~ ..... §... (1) S '< >= 0 0- '< ::r: ~ tv Vl ° TH3 CH3 N CH30 CH30 H2C=CH~ H20, KCI CH3CH=CH-Q-0CH3 Hg(OAc)2 H20 10-12d Hg(OAc)2 CH3CH=CH~ CH30 H20 2 weeks Hg(OAc )2 CH 30 C6HsCH=CHOCH2CH3 CH30 CIHgCH2CHOH~ CH30 XHgCH(C6HS)CHO X = CI (88), Br (55) H20/acetone 6 HgX 2 /HgO (66) 79 (50) Hg(CH2COC6HS)2 H20/EtOH RT HgO/Hg(OAc)2 CH30 CH3CHOH~ CH30 CH3CHOHCHOH-D-0CH3 106 (86) AcOHgCH2COC6Hs H2O Hg(OAc)2 H2C=C(O C2HS)C 6Hs CIHgCH2CHOHCH2-Q-0CH3 H20, NaCI Hg(OAc)2 110 102, 103,109 109 106 104 103 ACOHgCH2CHOHCH2-Q-0CH3 108 107 Ref.

2. (continued) ::l 0' ~ §.... S CD 6~ '< ::r: ..... 3. H9CIO, ""OH CJ.. H9OAC ""OH Organomercur ial (s) (% Yield)o NoSH, No SO, NoSH,/NoOH NoSH, Subsequent reactants (961 > (911 95 (1001 % HzC=C(CH3 I COH (CH3 12 6 OH 9H ~D 6 OH CH3CO-<] Hg' trans HOCHzCHzOH (-1001 + HCOCHO (-1001 ITOH Product(s) (% Yield)o 132 128 34 39,40 131 129, 130 109 129 128 127 Ref. 1 H20ITHF HglOAclz 196, 991 1:1 H20ITHF 11-15min RT HgiOAcl2 HgBr 139 39, 40 138 H20 15mln, KBr HglOAc 12 a'OH 136, 137 39, 40 133 133 H CXO ", HgCl OH &OH H20, NoCI 6 1931 11 + CH3 Ref.

Continued) 76 HO CH3 CH3 > 24 CH3 ,CH3 (-100 total) (9510101) OH 58 > 'CH3 CH30~ 66 CH3 42 "'CH3 0, HO, 34 (-10010101) HCJ3 CH3 CH36 CH3 > (-100 lolali CH3 ,OH (80) 4 OH(Ae) I C02C2HS 0 ° (65-75) 6 "OH A A CH3 96 6''''OH> OH(Ae) 6" OAe Product(s} (Of. Yield}a 155, 156 147, 155, 156 148 154 71 142 144 153 Ref. j:>. 3. /NaOH NaBH 4 /NaOH NaBH4/NaOH NaBH4/NaOH Subsequent reactants 6 83 32 CH3 OH 0 0 OH H3 ' CH 3 ,OH (88) 17 c=J:~"CH3 CH3 Q ""CH; CHj'" 58 HO 45 HOO~,~3 CH3:aOH CH{' CH3 OH + ' CH 3 CH3QOH 54 CH30:~ Product(s) (% Yield)a 159 159 39,40 128 159 155 157, 158 147 147 Ref.

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