Ring Expansion/Contraction Reactions Contractions.pdf6π-Electrocyclic Reactions: One of Three...

Ring Expansion/Contraction ReactionsLecture Notes

General Reviews:L. F. Silva, Tetrahedron 2002, 58, 9137.

Wagner-Meerwein Rearrangements/Carbocations:X. Criery, Chem. Rev. 1991, 91, 1625.

Grob Fragmentations:C. A. Grob, P. W. Schiess, Angew. Chem. Int. Ed. 1967, 6, 1.

Pinacol Rearrangements:Z.-L. Song, C.-A. Fan, Y.-Q. Tu, Chem. Rev. 2011, 111, 7523.

Wolff Rearrangements:W. Kirmse, Eur. J. Org. Chem. 2002, 2193

Ring Contractions/Expansions: Why Bother?

D. L. Boger, C. M. Baldino, J. Am. Chem. Soc. 1993, 115, 11418.

CO2MeCO2Me

MeOMeO

CO2MeMeOMeO

-[NH3](68%)

CO2MeCO2Me

MeOMeO

H2N NH

CO2MeCO2Me

MeOMeO

CO2HMeOMeO

NaH, MeI, DMF

CO2MeMeOMeO

(100%)LiOH

Reductivecleavage

Zn,HOAc

Enamine-Iminecondensation

22 °C,24 h

Electrocyclization Cascades:Black's Hypothesis for the Biosynthesis of the Endiandric Acids

D. St. C. Black and co-workers, Aust. J. Chem. 1982, 35, 2247.

PhCO2H

HO2CPh

endiandric acid D

endiandric acid E

Diels-Alderreaction

A = conrotatory 8πelectrocyclization

B = disrotatory 6πelectrocyclization

endiandric acid A

4π-Electrocyclic Reactions:Part of a Total Synthesis of Periplanone B

S. L. Schreiber, C. Santini, J. Am. Chem. Soc. 1984, 106, 4038.For a review, see: Classics in Total Synthesis I, Chapter 21

175 °C, toluene

periplanone B

Oxy-Coperearrangement

4π-conrotatoryelectrocyclicring opening

KH,18-Crown-6

18-crown-6

Olefin isomerization

6π-Electrocyclic Reactions:Erasure of the Ring-Opened Product

E. J. Corey, A. G. Hortmann, J. Am. Chem. Soc. 1965, 87, 5736.

dihydrocostunolide

Me H hν, MeOH,-18 °C

Al(Oi-Pr)3,i-PrOH, Δ

Al2O3,pyridine,

220 °C

LiBr,DMF,

120 °C

What is the name reaction in the second step?

H2,Raney NiMeOH,-18 °C

6π-conrotatoryelectrocyclicring opening

25 °C

6π-disrotatoryelectrocyclization

6π-Electrocyclic Reactions:One of Three Pericyclic Reactions in a Colchicine Total Synthesis

A. Eschenmoser and co-workers, Helv. Chim. Acta 1961, 44, 540.

MeOMeO

Diels-Alderreaction

MeOMeO

norcaradiene derivative

MeOMeO

colchicine

RetroDiels-Alder

reaction

-[CO2]

t-BuOK

1. MeOH, H2SO42. CH2N2

6π-disrotatory electrocyclic ring openings are often referred to as norcaradiene rearrangements

6π-dis-

rotatoryopening

25 °C

Oxidative Ring Expansions

P. A. Wender and co-workers, J. Am. Chem. Soc. 1997, 119, 12976.

mCPBA,THF,

0→25 °C,12 h

Ac2O,4-DMAP,

py, 0 °C,10 min

[Ketalization](100%)

K. Iida and co-workers, FEBS 2007, 274, 3475.

MeCO2H

CO2MeMeO2C

HO2CMe

MeHO2C

precorrin core

MeCONH2

CONH2RHNOC

MeH2NOC

vitamin B12

T. Narender and co-workers, J. Nat. Prod. 2010, 73, 747.

BzOH OAcO

OHAcOMe

HOTaxolTM

OAcAcOMe

BF3•OEt2

abeotaxane frameworktaxane framework

Progesterone: A Critical Steroid

progesterone

ClClTFA, 0 °C

progesterone

ClClTFA, 0 °C

Drugs of the Future?

with A. P. Brucks, D. S. Treitler, I. Moga, J. Am. Chem. Soc. 2012, 134, 17714.

NH2 HN

NHNH2N

•H2SO4

Octaporphyrin[30 electron system, n = 7]

Cyclopamine

Drugs of the Future?

with A. P. Brucks, D. S. Treitler, I. Moga, J. Am. Chem. Soc. 2012, 134, 17714.

NH2 HN

NHNH2N

•H2SO4

Octaporphyrin[30 electron system, n = 7]

Cyclopamine

A. Giannis and co-workers, J. Am. Chem. Soc. 2010, 132, 9968.

NTf Tf

74% 22%

H HMeO

NTf Tf

39% 41%

A. Giannis and co-workers, J. Am. Chem. Soc. 2010, 132, 9968.

NTf Tf

74% 22%

H HMeO

NTf Tf

39% 41%

H.-G. Schmalz and co-workers, Org. Lett. 2012, 14, 3692.

What other productscould have formed?

BF3•OEt2

MeOH,CH2Cl2

E. M. Carreira and co-workers, J. Am. Chem. Soc. 2002, 124, 14826.

MeNHNO

strychnofoline

IN OTBDPS

OTBDPS

BnO(55%)

Wagner-Meerwein Rearrangements

E. M. Carreira and co-workers, J. Am. Chem. Soc. 2002, 124, 14826.

OH[1,2-alkyl

shift]

Can you devisea mechanism

for the openingoperations?

Wagner-Meerwein Rearrangements

A. B. Smith and co-workers, J. Org. Chem. 1984, 49, 4094.

THF,50 oC

quadrone

[1,2-alkylshift]

Pinacol Rearrangements for Ring Contractions and Expansions

P. G. Harran and co-workers, Angew. Chem. Int. Ed. 2001, 40, 4765.

conc.H2SO4

40%H2SO4

OHHO O

Original discovery [R. Fittig, 1860]

Controlling product distribution [S. Danilov, 1917]

Key mechanistic consideration: diol/epoxide equilibrium

protic acid or Lewis acid conditions

conc.H2SO4

40%H2SO4

OHHO O

Original discovery [R. Fittig, 1860]

Controlling product distribution [S. Danilov, 1917]

Key mechanistic consideration: diol/epoxide equilibrium

protic acid or Lewis acid conditions

OHOHOH

OHOHOHOH

O(93%) (7%)

O(97%) (3%)

aq.HClO4

OHOHOH

OHOHOHOH

O(93%) (7%)

O(97%) (3%)

aq.HClO4

Pinacol Rearrangements for Ring Contraction

originally proposed structure of diazonamide AHO

revised structure of diazonamide A

CBzHNH

ONBocHN

OH2ArO

Br+1. p-TsOH

(3.0 equiv), toluene, 95 oC, 40 min2. N-(benzyloxy- carbonyloxy)- succinimide

(54%overall)

Pinacol Rearrangements for Ring Expansion

P. S. Baran and co-workers, Science 2013, 341, 878.

MeMeHO

OOO Me

OH phorbol

HOHOOH

MeMeMe

HO ingenol putative intermediate

BF3•OEt2(10 equiv),

CH2Cl2-78 oC to

-40 oC, 30 min(80%)

HOHOOH

MeMeMe

HO ingenol

MeMeMe

OTBSOOO

P. S. Baran and co-workers, Science 2013, 341, 878.

MeMeHO

OOO Me

OH phorbol

HOHOOH

MeMeMe

HO ingenol putative intermediate

BF3•OEt2(10 equiv),

CH2Cl2-78 oC to

-40 oC, 30 min(80%)

HOHOOH

MeMeMe

HO ingenol

MeMeMe

OTBSOOO

Semi-Pinacol Rearrangements for Ring Contractions and Expansions

R RHO RM

XX = OMs, OTs, Cl, Br, I,

N2+, SR, SeR, etc.

Bronsted acid or baseR R

nO σ*C-C (app)σC-C σ*C-X (app)

HO RMR

Electrophiles for intramolecular cases:oxocarbeniums, thiocabeniums, iminiums

Electrophiles for intermolecular cases:haloniums, seleniums, proton, Lewis acids

Pinacol Rearrangements for Ring Expansion/Contraction

J. K. Cha and co-workers, Angew. Chem. Int. Ed. 2005, 44, 121.Tanino and co-workers, J. Am. Chem. Soc. 2003, 125, 1498.

AlMe3,CH2Cl2

-78 to 0 oC

(82%)89

MeMeMe

AlMe3,CH2Cl2

(76%over

2 steps)

AlR = TIPS

MeMeMe

Pinacol Rearrangements for Ring Expansion/Contraction

J. K. Cha and co-workers, Angew. Chem. Int. Ed. 2005, 44, 121.Tanino and co-workers, J. Am. Chem. Soc. 2003, 125, 1498.

AlMe3,CH2Cl2

-78 to 0 oC

(82%)89

MeMeMe

AlMe3,CH2Cl2

(76%over

2 steps)

AlR = TIPS

MeMeMe

J. S. Kingsbury and E. J. Corey, J. Am. Chem. Soc. 2005, 127, 13813.

AlMe3,toluene,CH2Cl2,

4 oC(90%)

OCH2SMe

AlHMe3

β-araneosene

MsCl,CH2Cl2,

-30 to 4 oC

J. S. Kingsbury and E. J. Corey, J. Am. Chem. Soc. 2005, 127, 13813.

AlMe3,toluene,CH2Cl2,

4 oC(90%)

OCH2SMe

AlHMe3

β-araneosene

MsCl,CH2Cl2,

-30 to 4 oC

Pinacol Rearrangements for Ring Contraction

Y. Kita and co-workers, J. Am. Chem. Soc. 2001, 123, 3214.

CpO2COMeOMe

BF3•Et2OCH2Cl2, 0 oC

CpO2COMeOMe

(94%) N

OMeOMe

Cp = (1S)-(_)-camphanic acid

fredericamycin A

H. Nemoto and co-workers, J. Chem. Soc. Perkin Trans. 1 2000, 16, 2629.

OH Pd(OAc)2,HMPA/

THF (1:4)

O HX2Pd

(60%)(2.7:1 A:B)

equilenin A B

Semi-Pinacol Rearrangements for Ring Expansion

F. D. Toste and co-workers, Org. Lett. 2008, 10, 4315.

HO AuPPh3Cl (3 mol %),AgSbF6 (3 mol %),

CH2Cl2, 25 oC

OMePdCl2(CH3CN)2

DDQ, THF(70%)

H (±)-ventricosene

Grob Fragmentations

C. A. Grob, P. W. Schiess, Angew. Chem. Int. Ed. Engl. 1967, 6, 1.

a b c d x

electrofuge nucleofuge

a b c d x+ +

Grob Fragmentations

C. A. Grob, P. W. Schiess, Angew. Chem. Int. Ed. Engl. 1967, 6, 1.

a b c d x

electrofuge nucleofuge

a b c d x+ +

Grob Fragmentations for Ring Expansion

E. J. Corey and co-workers, J. Am. Chem. Soc. 1964, 86, 485

[Grobfrag-

mentation]

MeMe MeH H H

caryophyllene

Grob Fragmentations

L. A. Paquette and co-workers, J. Am. Chem. Soc. 2002, 124, 6542.

1. MsCl

2. KOt-Bu

MeMeMe

H(98%)

MeMeMe

Ojatrophatrione

Grob Fragmentations

J. D. Winkler and co-workers, Org. Lett. 2003, 5, 1805.

OK2CO3

DMF,75 oC

OH MeI,Ag2O

core of eleutherobin

Benzylic Acid Rearrangements in Total Synthesis

K. Gademann and co-workers, Chem. Eur. J. 2010, 16, 7692.

Otaiwaniaquinoid framework

LiHMDSTHF,

-15 oC

R = OMe6%

R = H65%

Benzylic Acid Rearrangements in Total Synthesis

K. Gademann and co-workers, Chem. Eur. J. 2010, 16, 7692.

Otaiwaniaquinoid framework

LiHMDSTHF,

-15 oC

R = OMe6%

R = H65%

Favorskii Rearrangements in Synthesis

H. O. House and co-workers, J. Org. Chem. 1965, 30, 2948.

Favorskii Rearrangements in Synthesis

H. Takeshita and co-workers, J. Org. Chem. 1994, 59, 6490.

KOH;acid

"Quasi-Favorskii" Rearrangement for Ring Contraction

M. Harmata and S. Wcharasindhu, Org. Lett. 2005, 7, 2563.

BrMeMe

LiOBr +

THF,-78 oC

Me-30 oC

(90%) O

(from [4+3]reaction)

AcOCO2Me

tricycloclavulone

Ring Contraction of Cross-Conjugated Dienones

K. C. Nicolaou and co-workers, Angew. Chem. Int. Ed. 2001, 40, 3679.

Osantonin

isophotosantoniclactone

Dozensof

natural products

AcOH/H2O

Ring Contraction of Cross-Conjugated Dienones

Osantonin

isophotosantoniclactone

Dozensof

natural products

AcOH/H2O

Norrish Type-1 Cleavage Pathways

MeO OO

Wolff Rearrangements

L. Wolff, Liebigs Ann. Chem. 1902, 325, 129.

ON N Ag2O,

[or hv, H2O]

ON N O

O• O

Ag2O or hνH2O

L. Wolff, Liebigs Ann. Chem. 1902, 325, 129.

ON N Ag2O,

[or hv, H2O]

ON N O

O• O

Ag2O or hνH2O

The Wolff Photochemical Rearrangement

V. Mascitti, E. J. Corey, J. Am. Chem. Soc. 2004, 126, 15664.For a review, see: W. Kirmse, Eur. J. Org. Chem. 2002, 2193.

N2•O

CO2MeCO2H

pentacycloanemmoxic acid

MeOH, 2 h

P. A. Grieco and co-workers, J. Am. Chem. Soc. 1999, 122, 9891.L. N. Mander and co-workers, J. Am. Chem. Soc. 1997, 120, 3828.

MeOMOM

H O OMe

MeOMOM

1. NaH, HCO2Et2. TsN3

3. hν, MeOH(48%)

BnO2C H

hν, MeOH O O

BnO2C H CO2Me(79%)

P. A. Grieco and co-workers, J. Am. Chem. Soc. 1999, 122, 9891.L. N. Mander and co-workers, J. Am. Chem. Soc. 1997, 120, 3828.

MeOMOM

H O OMe

MeOMOM

1. NaH, HCO2Et2. TsN3

3. hν, MeOH(48%)

BnO2C H

hν, MeOH O O

BnO2C H CO2Me(79%)

Wolff Rearrangement Strategy to Access Dolabellatrienone

OHCO2Me

dolabellatrienone

[Wolffrearrangement]

LDA, -78 °C, THF;O2, P(OEt)3

2. NaIO4 on silica gel

1. NaHMDS, -78 °C, THF; HCO2Et, -78→0 °C

(82% overall)

hν, 450 W,MeOH,

25 °C, 2 h2. TsN3, Et3N CH2Cl2

MeMe (86% overall)

1. LiAlH4

OHCO2Me

dolabellatrienone

[Wolffrearrangement]

New Wolff Rearrangement Strategy to Access Dolabellanes

H O ON2

New Wolff Rearrangement Strategy to Access Dolabellanes

[Wolffrearrange-

CO2MeCO2Me

severalnatural

products

H O(79%)

LiHMDS,-78 °C, THF;

TMSCl;IBX•MPO,

DMSO, 25 °C(79%)

Trisyl azide,BnEt3NCl,

18-Crown-6.benzene/

66% aq.KOH,45 °C, 48 h

K. C. Nicolaou, T. Montagnon, P. S. Baran, Angew. Chem. Int. Ed. 2002, 41, 993.L. Lombardo, L. N. Mander, Synthesis 1980, 368.

hν, 450 W,MeOH,

25 °C, 2 h

(79%)[Wolff

rearrange-ment]

TMSCl;IBX•MPO,

DMSO, 25 °C(79%)

18-Crown-6.benzene/

66% aq.KOH,45 °C, 48 h

hν, 450 W,MeOH,

25 °C, 2 h

(79%)[Wolff

rearrange-ment]

CO2MeCO2Me

TMSCl;IBX•MPO,

DMSO, 25 °C(79%)

18-Crown-6.benzene/

66% aq.KOH,45 °C, 48 h

DBU,115 °C, 18 h

Wolff Rearrangement Strategy to Access Dolabellanes

H(67%)

E. J. Corey, R. S. Kania, Tetrahedron Lett. 1998, 39, 741.J. S. Kingsbury, E. J. Corey, J. Am. Chem. Soc. 2005, 127, 13813.

OHpalominol

dolabellatrienone

MeLi,THF, -20°C

PDC,4 A M.S.

CH2Cl2, 25°C(92%)

H(67%)

OHpalominol

dolabellatrienone

1. L-Selectride2. LDA, O23. LiAlH4, NaIO4

(51%overall)

MeLi,THF, -20°C

PDC,4 A M.S.

CH2Cl2, 25°C(92%)

H(67%)

OHpalominol

dolabellatrienone

HMe MeO

1. L-Selectride2. LDA, O23. LiAlH4, NaIO4

(51%overall)

1. MOMI, i-Pr2NEt, THF, Δ, 12 h2. Li/NH3

β-araneoseneisoedunol

MeLi,THF, -20°C

PDC,4 A M.S.

CH2Cl2, 25°C(92%)

Et2O, -78°C(82%) (92% overall)

Planned Synthetic Approach to Presilperfolan-8-ol

with P. Hu, J. Am. Chem. Soc. 2017, 139, 5007.

H LDA,Br

(90%)(5:1 dr)

[6 gram scale]

H KHMDS; Comins'reagent(86%)(5:1 rr)

[7 gram scale]

MeMeMe

presilphiperfolan-8-ol

[RingContraction]Me

Pd(OAc)2 (10 mol %),DPEPhos (20 mol %),

Et3N (2 equiv), toluene, 0.1 M, 110 °C

[2 gramscale]

3 steps

[gram scale]

(28% over4 steps)

13 step total synthesis of moleculeFirst 10 steps performed on gram scale

[1 step from(R)-pulegone]

Use of the Wolff Rearrangement to Afford a trans-Fused [3.3.0]-Bicyclooctane

HOH p-ABSA,DBU Me

HOR N2

CO2Me*MeMe

CHOMeMe

(95% over2 steps)

HORTMSOTf,Et3N

R = TMS

>800 mg prepared

[Wolffrearrange-ment]

HOH p-ABSA,DBU Me

HOR N2

CO2Me*MeMe

CHOMeMe

(95% over2 steps)

HORTMSOTf,Et3N

R = TMS125 W Hg UV-lamp,

>800 mg prepared

HOH p-ABSA,DBU Me

HOR N2

DIBAL-H;t-BuOH,

Dess-Martinperiodinane Me

CO2Me*MeMe

CHOMeMe

(95% over2 steps)

HORTMSOTf,Et3N

>800 mg prepared

HOH p-ABSA,DBU Me

HOR N2

DIBAL-H;t-BuOH,

Dess-Martinperiodinane

1. Rh(PPh3)3Cl2. TBAF Me

CO2Me*MeMe

CHOMeMe

(95% over2 steps)

(93%)(40% over2 steps)

HORTMSOTf,Et3N

>800 mg prepared

Ring Contractions/Expansions: Take-Home Challenge

H.-G. Schmalz and co-workers, Org. Lett. 2012, 14, 3692.

The Laurencia Family of Haloethers:An Open Biogenetic Question for their Formation

Me OAc

laurefucinlaurencin

laurallene

Fujiwara, K. “Total Synthesis of Medium-Ring Ethers from Laurencia Red Algae” in Topics in Heterocyclic Chemistry (Vol. 5), Kiyota, H. (Ed.), Springer-Verlag: Berlin, 2006, pp. 97-148.

laureoxanyne

First member isolated in 1965 by IrieOver 150 members total

Largest subset (>50 members) have 8-membered bromoetherTotal and Formal Syntheses of Laurencin: Murai, Overman, Palenzuela, Holmes,

Hoffmann, Crimmins, Yamamoto, Kim, Fujiwara, Pansare, OrtegaOther Syntheses: Overman, Crimmins, Fujiwara, Boeckman, Hoshi, Kim, Takeda

Me OAc

laurencin

Fujiwara, K. “Total Synthesis of Medium-Ring Ethers from Laurencia Red Algae” in Topics in Heterocyclic Chemistry (Vol. 5), Kiyota, H. (Ed.), Springer-Verlag: Berlin, 2006, pp. 97-148.

HO OPivO

O OPiv

Pb(OAc)4

Murai and co-workers, Tetrahedron Lett. 1992, 33, 4345.

Overman and co-workers, J. Am. Chem. Soc. 1995, 117, 5958.

Crimmins and co-workers, J. Am. Chem. Soc. 1999, 121, 5653.

33 linearsteps total

Me OPiv

Me OAc

laurencin

23 linearsteps total

BF3•OEt2,t-BuOMe

AcO OTBDPSOBr

Me OAc

laurencin

AcO OTBDPS(97%)

24 linearsteps totalGrubbs 1

Murai, A. “Biosynthesis of Cyclic Bromoethers from Red Algae” in Comprehensive NaturalProducts Chemistry (Vol. 1), Sankawa, U. (Ed), Elsevier: New York, 1999, pp. 303-324.

crudebromo-

peroxidase

0.015%(0.085%brsm)

laurediol deacetyllaurencin

Murai and co-workers, Chem. Lett. 1994, 2307

OHlaurediol

"Br " * 8-memberedbromoether

naturalproducts

Our alternative hypothesis:

Murai, A. “Biosynthesis of Cyclic Bromoethers from Red Algae” in Comprehensive NaturalProducts Chemistry (Vol. 1), Sankawa, U. (Ed), Elsevier: New York, 1999, pp. 303-324.

crudebromo-

peroxidase

0.015%(0.085%brsm)

laurediol deacetyllaurencin

Murai and co-workers, Chem. Lett. 1994, 2307

OHlaurediol

"Br " * 8-memberedbromoether

naturalproducts

Our alternative hypothesis:

Value and Challenges of a Bis-Oxonium Biosynthetic Intermediate

with D. S. Treitler, A. P. Brucks, W. Sattler, J. Am. Chem. Soc. 2011, 133, 15898.

laurefucin

deacyllaurencinOH

HOMe OH

laurediolMe OH

"Br " "Br "

[loss of Br ]

laurefucin

deacyllaurencinOH

HOMe OH

laurediolMe OH

"Br " "Br "

[loss of Br ]

laurefucin

deacyllaurencinOH

laureioxanyne

HOMe OH

laurediolMe OH

"Br " "Br "

[loss of Br ]

[intramolecularcyclization]

laurefucin

deacyllaurencinOH

laureioxanyne

HOMe OH

laurediolMe OH

"Br " "Br "

[loss of Br ]

[intramolecularcyclization]

[external nucleophileand SN2]

Ring Expansion/Contraction Reactions Contractions.pdf6π-Electrocyclic Reactions: One of Three...

Documents

Transcript of Ring Expansion/Contraction Reactions Contractions.pdf6π-Electrocyclic Reactions: One of Three...

Chemical Reactions Types of Reactions Synthesis reactions Decomposition reactions Single displacement reactions Double displacement reactions.

Simple chemical reactions Chemical change Reactions with acid Reactions with oxygen 7F 7F Simple chemical reactions.

Helvetica Chimica Acta 2015 Special Issue: Maoqun Tian ... · Albert Eschenmoser and Organic Synthesis as Art Albert and Elisabeth Eschenmoser The issue (December 2015, Volume 98,

The [3+2]Cycloaddition Reaction - University of Chicagosnyder-group.uchicago.edu/downloads/Lectures2020/The [3+2...The [3+2] Cycloaddition Reaction O O O Me Me OPMB XX Lecture Notes

Chemical Reactions. Types of Chemical Reactions Acid-Base Reactions Neutralization Reactions Neutralization Reactions In a reaction involving HCN(aq),

Coprecipitation Reactions Coprecipitation Reactions

2004 FINAL REPORT - ntrs.nasa.gov · 2004 FINAL REPORT THE C"RY OF EARLY ... Michael Meyer, Alex Rich, ... Albert Eschenmoser (ETH, Zurich and TSRI); Marina Fomenkova (UCSD); Antonio

7.3 Nuclear Reactions: Nuclear reactions are different than chemical reactionsNuclear reactions are different than chemical reactions Chemical Reactions.

Reactions of Alkenes: Addition Reactions

Aqueous Reactions General Properties of Aqueous Solutions -Electrolytes -Concentration -Dilutions Reactions - Precipitation Reactions - Acid-Base Reactions.

Ch 10- Radical Reactions. Radical Reactions All the reactions we have considered so far have been ionic reactions. Ionic reactions are ones where covalent.

Types of Reactions 1.Synthesis reactions 2.Decomposition reactions 3.Single displacement reactions 4.Double displacement reactions 5.Combustion reactions.

Section 8.2 Types of Chemical Reactions Combination Reactions Decomposition Reactions Single-Replacement Reactions Double-Replacement Reactions Combustion.

Reactions of alkenes: stereospeciﬁc reactions

1 Redox Reactions : HALF REACTIONS. 2 REDOX REACTIONS Day 1: Using Oxidation numbers Electrochemical Reactions REACTIONS.

By Noor Amirah Abdul Halim. Parallel reactions Series reactions Complex reactions (parallel and series reactions) Independent reactions.

In Copyright - Non-Commercial Use Permitted Rights ...21806/eth-21806-01.pdf · Meinem Lehrer, Herrn Prof. Dr. A. Eschenmoser, unter dessen Leitung ich die vorliegende Promotions¬

Classifying Chemical Reactions Oxidation-Reduction Reactions Combination Reactions Decomposition Reactions Displacement Reactions Metathesis Reactions.

Chapter 1 Reactions of Organic Compounds Reactions ...nschemistry12.wikispaces.com/file/view/9+-+Reactions+of+Organic... · Chapter 1 – Reactions of Organic Compounds Reactions

Types of Chemical Reactions Single Replacement Reactions Double Replacement Reactions Combustion Reactions.