Compendium of Organic Synthetic Methods, Volume 8

648 Pages·1995·24.576 MB·English

Compendium of Organic
Synthetic Methods
Compendium of Organic
Synthetic Methods
Volume
8
MICHAEL 6. SMITH
DEPARTMENT CHEMISTRY
OF
THE UNIVERSITY OF CONNECTICUT
STORRS, CONNECTICUT
A Wiley-lnterscience Publication
JOHN WILEY 81 SONS, INC.
NewYork Chichester Brisbane Toronto Singapore
Cover illustration was adapted from "Disconnect By the Numbers: A Beginner's Guide to
Synthesis" by M. B. Smith. Journal of Chemical Educetion, 1980, 67, 848-856.
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10 9 8 7 6 5 4 3 2
DEDlC AT10 N
This book is dedicated to Dr. Ted Hoffman, who recently retired as Senior
Editor at Wiley-lnterscience after a long and distinguished career. Ted was
responsible for getting the Compendium started and for keeping it going for
more than twenty years. The many books and series for which Ted served as
editor have contributed enormously both to chemical education and to
chemical research. It would be difficult to find a bookshelf in an organic
chemistry research lab anywhere in the world that does not contain one or
more of the books for which Ted served as editor. a more personal level,
On
the publication of Volume 6 of this series in 1988 began my career as an
author, and many new opportunities have been opened to me because of
this. There are certainly many others who can similarly thank Ted.
Iw ant to use this dedication to thank Ted for his help to me, for his help to
the previous authors of the Compendium, and for his contributions to the
chemistry community in general (particularly the organic chemistry com-
munity). Those contributions are many and important. Thank you, and good
luck in your retirement.
MICHAE6L. SMITH
V
PREFACE
Since theoriginal volume in thisseries by Ian and Shuyen Harrison, thegoal
of the Compendium of Organic Synthetic Methods was to facilitate the
search for functional group transformations in the original literature of
Organic Chemistry. In Volume 2, difunctional compounds were added and
this compilation was continued by Louis Hegedus and Leroy Wade for
Volume3 of theseries. Wade became theauthor forVolume4 and continued
with Volume 5. I began editing the series with Volume 6, where I introduced
an author index for the first time and added a new chapter (Chapter 15,
Oxides). Volume 7 introduced Section (Oxides-Alkynes) through Sec-
378
tion 390 (Oxides-Oxides). The Compendium is a handy desktop reference
that will remain a valuable tool to the working organic chemist, allowing a
“quick check” of the literature. It also allows one to “browse” for new reac-
tions and transformations that may be of interest. The body of organic litera-
ture is very large and the Compendium is a focused and highly repre-
sentative review of the literature and is offered in that context.
Compendium of Organic Synthetic Methods, Volume 8, contains both
functional group transformations and carbon-carbon bond forming reac-
tions from the literature appearing in the years 1990, 1991, and 1992. The
classification schemes used for Volumes 6 and 7 have been continued.
Difunctional compounds appear in Chapter 16. Theexperienced user of the
Compendium will require no special instructions for the use of Volume 8.
Author citations and the Author Index have been continued as in Volumes 6
and 7.
Every effort has been made to keep the manuscript error free. Where
there are errors, I take full responsibility. If there are questions or com-
ments, the reader is encouraged to contact me directly at the address,
phone, fax, or E-mail addresses given below. Note that the phone and fax
area code for this section of Connecticut is tentatively scheduled to change
in 1996 to (860).
The manuscript for Volume 8 was prepared on a Macintosh-llciTMP C
using Microsoft Word” (version 5.1) for word processing. All structures
were prepared using ChemDraw” (version and the manuscript was
3.1)
printed with a Laserwriter” II printer. The graph presented in the introduc-
tion was prepared using Cricket-Graph.”
vii
viii PREFACE
As I have throughout mywriting career, 1 want to thank my wife Sarah and
my son Steven, who have shown unfailing patience and devotion during this
work. I also thank Carla Fjerstad, who edited this volume and was re-
Ms.
sponsible for its publication.
MICHAEBL. SMITH
University of Connecticut
Department of Chemistry
215 Glenbrook Rd., Room 151
Storrs, CT USA 06269-3060
Voice Phone: [phone]
Fax: [phone]
E-mail: [email protected]
CONTENTS
ABBREVIATIONS xi
INDEX, MONOFUNCTIONAL CO APO J IDS xv
INDEX, DIFUNCTIONAL COMPOUNDS xvi
INTRODUCTION xvii
1 PREPARATION OF ALKYNES 1
PREPARATION OF ACID DERIVATIVES AND
2
ANHYDRIDES 6
3 PREPARATION OF ALCOHOLS 16
4 PREPARATION OF ALDEHYDES 54
5 PREPARATION OF ALKYLS, METHYLENES AND ARYLS 66
6 PREPARATION OF AMIDES 117
7 PREPARATION OF AMINES 139
8 PREPARATION ESTERS 166
OF
9 PREPARATION OF ETHERS, EPOXIDES AND
THIOETHERS 184
10 PREPARATION OF HALIDES AND SULFONATES 200
11 PREPARATION OF HYDRIDES 210
12 PREPARATION OF KETONES 220
13 PREPARATION OF NITRILES 242
14 PREPARATION OF ALKENES 247
15 PREPARATION OF OXIDES 267
16 PREPARAflON OF DIFUNCTIONAL COMPOUNDS 276
AUTHOR INDEX 561
IX
ABBREVIATIONS
Ac Acetyl
Acetylacetonate
acac
AIBN azo-bis-I sobu tyronilrile
Aqueous
9-Borabicyclo[3.3.1J nonyl
9-BBN
9-Borabicyclo[3.3.l]nonyl
BINAP 1'-binapthyl
2R,3S-2,2'bis-(diphenylphosphino)-11
Bn Benzyl
Benzoy 1
Bz
0
BOC t-B utoxycarbo~~yl
)(lotau
BPY (BiPY) 2,T-Bipyridyl
Bu n-Butyl
CAM Carhxamidometliyl
CAN Ceric ammonium niuate
C- Cyclo-
Cat. Catalytic
0
Cbz Carbobenzyloxy
+OCH2Ph
Chirald
2S,3R-(+)-4-Dimelhylamin1o,-2 -diplienyl-3-me(hylbutan-2-ol
COD 1, S-Cyclooc~xlienyl
COT 1,3,S-Cyclooctatrieny1
CP Cy clopentadien yl
CSA Camphorsulfonic acid
CrAB cetyltrimethylammonium bromide C@j3NMe3+ Br-
Cy (c-C~H1 1 ) Cy clohex yl to
"C Temperature in Degrees Centigrade
DABCO
1,4-Diazahicyclo[2.2.2]octa11e
Dba Dibenzy lidene acetone
DBE 1,2-Dibrornoethane BICH2CH2Br
DBN 1
,S-Diazabicyclo[4.3.0]non-S-ene
DBU
1,8-Diazabicyclo[S.4.0]undec-7-ene
DCC 1,3-DicycloIicxylcarbodiimide c-C@ 1~-N=C=1N-C-C&3I
DCE I ,2-DichIorcleUiruie ClCH2CH2CI
xi
xii ABBREVIATIONS
DDQ 2,3-Dichloro-5,6-dicyano-l,4-benzoquinone
% de % Diastereomeric excess
DEA Diethy lamine HN(CH2CW2
DEAD Diethy lazodicarboxy late Et02C-N=NC02Et
Dibal-H Diisobutylaluminum hydride (Me2CHCH2)2AlH
Diphos (dppe) Ph2PCH2CH2PPh2
1,2-6is-(Diphenylphosphino)ethane
Diphos-4 (dppb) 1,4-bis-(Diphenylphosphino)butane Ph2P(CH2)4PPh2
DMAP 4-Dimethylaminopyridine
DME Dmethoxyethane MeOCH2CHzOMe
DMF N,N'-Dimethy lformamide
DmP bis-[1 ,3-Di@-rnethoxyphenyl)- 1,3-propanedionatoI
DPm Dipivaloylmethanato
DPPb 1.4 -bis-(Diphenylphosphino)butane Ph2P(CH2)4PPh2
DDPe 1,2-bis-(Diphenylphosphino)ethane Ph2PCH2CHzPPh2
DpDf bis-(Dipheny 1phosphino)ferrocene
DPPP 1,3-bis-(DiphenyIpliosphino)propane PhzP(CH213PPh2
Dvb Divinylbenzene
e' Electrolysis
%ee % Enantiomeric excess
1- Ethox yeth yl EtO(Me)CHO-
I 3
Et Ethyl -CH2CH3
EDA Erh ylenediamine H~NCH~CHZNH~
EDTA Erhylenediaminetetraacetic acid
FMN Flavin mononucleotide
Fod tris-(6,6,7,7,8,8,8)-Heptafluoro-2,2-dimethyl-3,5-oc~edio~te
FP Cyclopentadienyl-his-carboynl iron
FVP Flash Vacuum Pyrolysis
h Hour (hours)
hv Irradiation with light
1,5-HD 1,5-Hexadienyl
HMPA Hexamethy lphosphoramide (MeW2P-O
HMPT Hexamethylphosphoxus triamide tMe3W3P
Isopropyl -CH(CH3)2
iPr
LICA (LIPCA) Lithium
cyclohexylisopropylamide
LDA Lithium diisopropylamide LiN(iPr)2
LHMDS Lithium hexamethyldisilazide LiN(SiMe3h
LTMP Lithium
2,2,6,6-tetramethylpiperidide
MABR Methylaluminum
bis-(4-bromo-2,6-di-tert-butylphenoxide)
MAD bis-(2,6-Di-t-bu aluminum
tyl-4-melhy1phenoxy)methyl
mCPBA meta-Chloroperoxybenzoica cid
Me Methyl -CH3
MEM P-Methoxy etiloxy meth yl MeOCH2CW2OCHz-
Mes Mesityl 2,4,6-tri-Me-C6H2
ABBREVIATIONS xiii
MOM Methoxy meth yl MeOCH2-
Ms Methanesulf ony 1 CH3S02-
MS Molecular Sieves (3A or 4A)
MTM Methylthiomethyl MeSCH2-
NAD Nicotinamide adenine dinucleotide
NADP Sodium triphosphopyridine nucleotide
Napth Naphthyl (CioH7)
NBD Norbomadiene
NBS N-Bromosuccinimide
NCS N-Chlorosuccinimide
NIS N-I odosuccinimide
Ni(R) Raney nickel
Oxone 2 KHSOyKHSOq*K2S04
@ Polymeric backbone
PCC Pyridinium chlorochromate
PDC Pyridinium dichromate
PEG Polyethylene glycol
Ph Phenyl
PhH Benzene
PhMe Toluene
Phth Phthaloyl
Pic 2-Pyridinecarbox y late
Pip Piperidyl
n-Propyl -CH2CHzCH3
Pr
PY Pyridine N 3
quant. Quantitative yield
Red-Al [(MeoCH2CH20)2AIH21Na
sBu sec-Butyl CH3CHaH(CH3)
sBuLi sec-Butyllithium CH3CH2CH(Li)CH3
Siamyl Diisoam yl [(CH3)2CHGH(CH3)-12
TASF tris-@iethylamino)sulfonium difluorotrimethy l silicate
TBAF Tetrabutylammonium fluoride n-BuqN+ F'
TBDMS t-Butyldimethylsily l f-Bu Me2Si
. .
TBHP (1-BuOOH) f-But&ydroperoxide Me3COOH
t-Bu tert-Butyl -C(CH3)3
TEBA Trieth ylbenzylamrnonium Bn(Et)3N+
TEMPO Tetramethylpi~ridinyloxyf ree radical
TFA Trifluoroacetic acid CF3COOH