Diol to alkene - thiophosgene with diol - thiocarbonate - :P(Ome)3 att S=C - cyclic carbene cyclises around elim CO2 to alkene
Thioketon w diazoR2 coupli alkene - R2C=N=N make episulf- :PPh3 desulfurises to alkene Diol to alkene - thiophosgene with diol - thiocarbonate - :P(Ome)3 att S=C - carbene cyclis Ketone w H2NNH2 then MnO2 or phenyliodine(III) diacetate into R2C=N[+]=N[-] diazo
Ketone into epox and ab unsat alkene into cyclopropane - sulfur ylides - 2 types - Me2S[+]-CH2[-] and Me2S(=O)[+]-CH2[-]
Ketone to alkene - Li[+][-]CH2SiMe3 non cleavable group - then either acid or base = acidify/H2O or depro :OH and either 2nd H2O attack Si kick in form alkene or O- atack Si 4 memb
Ketone to ab unsat ketone - IBX hypervalent - O:H att I
Ketone to alkene - use to bind two fragments one on ketone/aldehyde and one on sulfone - E alkene selective usually - PhS[O]2-CHLiR aka PhSO2CH2[-][+]Li - beta hydroxy sulfone, Ac'
Either Ketone to diol or ab unsat 1,4 attack (Cu cat) both adding -CH2OH unit - Li[+][-]CH2SiMe2-H or Ph or allyl cleavable group - then F[-] make Si[-] metal elim cleavable grp -
Ketone to TMS-Cl silyl enol ether aka ketone w alpha alc - epoxidise w mCPBA - :O-Si attack down rearranges to ketone w alpha-TMS - H2O elim TMS to ketone w alpha alc
Aldehyde to alkyne - via Ph3P-CBr2 via C=CBr2 via C=CBrLi - H migrates around - if 2eq BuLi = lithiated alkyne = attack
Alkene to Bromoalkane - HBr w peroxide - [.]OBz HAT w HBr into Br[.] att 1st alkene iin antimarkovnikov fashion = the peroxide effect is vs HBr ionic style H 1st via cc Br second
Alkene to di-subsitituted - R-X joins across alkene bond via radical chain - largest grp R goes on least hindered side of alkene - X = Cl, I, Br, SC(=S)OEt w peroxide initiator
Allylic or benzylic bromination -radical chain process - trace Br2 in NBS w hv or initiator - Br[.] remove allylic H into C=C-C[.] forms insitu HBr low conc - low HBr+NBS - in CCl4
Alkene-EWG w R-X via HSnBu3 AIBN system -
Alkene-EDG w EWG-R-X via HSnBu3 AIBN system - slow addition syringe pump w HSnBu3
I2 cat + cis alkene to trans alkene w heat/hv to 2I[.] temporarily binds to alkene into Iodo-radical - old alkene bond rotates trans - radical re att and reforms alkene elim I[.]
Alcohol to alkane - NaH depro alc, O- w CS2 and MeI into xanthate ester - HSnBu3 w AIBN init Sn[.] attack S kicks down make C=O and r-CH2[.] - aka Radical Reduction rxn
C Acid w SOCl2 then NaO-Pyr-ortho(=S) - HSnBu3 w AIBN heat Sn[.] attack S=C kicks down elim Bu3Sn-Pyr and R-C(=O)-O[.] collapse down CO2 and R[.] then rxn w H-SnBu3
R-I or Br or SePh or OC(=S)SMe or NO2 w HSnBu3 AIBN w heat = [.]SnBu3 attack X atom and RCH2[.] attack HAT H-SnBu3 to continue chain rxn HAT w X atom transfer
NaI I- attack R-Br in acetone, makes R-I and NaBr insolb crashes out
Ph3P: attack N=N of DEAD - onto C=O, -O attacks back down to acid H+, RO:H attack P, Nu- reattack C-O-P Sn2
S=O res to S-O-, S-O- attack C=O elim Cl-, Cl- reattack S+ elim CO CO2, RO:H attack S-Cl elim Cl-, Cl- reattack depro, :NEt3 attack S-CH3, S-CH2- depro O-CH2 to C=O elim DMS
Me2S: attack Cl-N of NCS, N- reattack S-Cl, RO:H attack S elim N, N- reattack depro, :NEt3 attack S-CH3 proton, C- depro O-C-H proton
N: of dmf kicks up O: attacks P=O, O- back down elim Cl, Cl- reattack C=N, N: kicks up elim O=P, Ar attack C=N+, N: kicks in elim Cl, WU H2O: attack C=N, O: attacks down and elim +
Ph3P: attacks end N of R-NNN:, N: attacks across P+ and kicks around elim N2, N: attacks up res, H2O: attack P=N, proton trans, O: attack down elim HNR makes P=O, N- reattacks and
C=O: protonates, N: attacks C=O, proton trans, N: attacks up elim H2O, enolised carbonyl O: attacks down to alkene and onto attack C=N
Ph3P: attack R-Br, Bu- or HO- depro alpha H, +P-C- attack C=O, 4 member O-P ring break down to P=O
C=O: coord to Mg, C=O bond attacks Mg and Mg-R bond attacks down to C=O, concerted, WU H3O+ O: protonates, H2O: attack Mg
Phthalamide depro w HO- kicks up to C=O, O- back down to R-Br, H2N:NH2 attacks C=O kicks up then down elim N-R, other N-N: attack second C=O elim -N-R
NaOH HO- depro R-OH, R-O- attack R'-Br
H2N:NH2 attack C=O, HO- depro inner H-N makes C=N, 2nd HO- depro outer N-H to N-, N- kicks down makes N=N-H, 3rd HO- depro N=N-H, N=N- kicks down again make N2 and C-, C- protonate
alpha diazo ketone res, -O kicks down into R group internal migrate to next carbon elim N2, form ketene
AC or Acyl anhydride w :NR2H or RO:H nucleophiles w base NaOH, :N attack C=O, O- kicks down elim Cl or Acyl, -B depro to give amide or ester
C=O: attack H-O-O mcpba, O- attack C=O, more electron rich R internal migrates to O-O and breaks, C=O kicks down depro 2nd mcpba, O: lp comes down to cc, O- depro ester
:NH2OH attack C=O, forms oxime, O: protonates w H+, R grp trans to OH2 LG internally migrates, R-(+)C=N-R tauto to R-CN(+)-R, H2O: attack C kicks into N+, C=N: protonate, O: lp kic
Na w NH3 free e-, e- SET to benzene, kicks down two C=C forms top anion - and bottom radical, C- protonates from EtOH, 2nd e- SET to bottom radical forms 2nd anion-, protonates, ED
nitroaryl w 3eq vinyl-grignard
Acyl azide res into O- form by -N: kick into (-)N-N(+)N then N: kicks up into C=O, -O-C kicks down internal R group migration to C=N and N2 elim gives isocyanate
CA protonates, RO:H attacks C=O, proton transfer, :O-R kicks down and elim H2O to give ester
C=O: protonates, PhNHNH2: attacks C=O, proton trans, N-N: kicks up to elim H2O, -Oac reattacks and depro alpha H to C=N, inner Ph-NH: protonates, N-N bond cyclises round, inner N:
Ph-Ester Ph-O: attack AlCl3, C=O: attack down elim R-CO+, Al-O:-Ph lp kicks down into ring and attacks R-CO+, H2O depro and rearomatise and breaks Al-O bond
CrO3 O: protonates from H3O+, H2O: attack Cr kicks into Cr=OH+, 2nd H2O: depro H2O-Cr make chromic acid, R-O:H attack Cr=O, H2O depro, Cr-O- kicks down and elim HO-, H2O: depro kic
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