Compendium of Organic Synthetic Methods

743 Pages·2014·41.54 MB·English

by  Michael B. Smith

Compendium of
Organic Synthetic Methods

Compendium of
Organic Synthetic Methods
Volume 13
Michael B. Smith
University of Connecticut
W I L EY
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10 9 8 7 6 5 4 3 2 1
TABLE OF CONTENTS
PREFACE vii
INTRODUCTION ix
INDEX, MONOFUNCTIONAL COMPOUNDS xvii
INDEX, DIFUNCTIONAL COMPOUNDS xix
ABBREVIATIONS xxi
ABOUT THE AUTHOR xxv
1 PREPARATION OF ALKYNES 1
2 PREPARATION OF ACID DERIVATIVES 13
3 PREPARATION OF ALCOHOLS AND THIOLS 21
4 PREPARATION OF ALDEHYDES 75
5 PREPARATION OF ALKYLS, METHYLENES, AND ARYLS 89
6 PREPARATION OF AMIDES 225
7 PREPARATION OF AMINES 259
8 PREPARATION OF ESTERS 303
9 PREPARATION OF ETHERS, EPOXIDES, AND THIOETHERS 325
10 PREPARATION OF HAL1DES AND SULFONATES 351
11 PREPARATION OF HYDRIDES 365
12 PREPARATION OF KETONES 371
13 PREPARATION OF NITRILES 399
14 PREPARATION OF ALKENES 409
15 PREPARATION OF OXIDES 433
16 PREPARATION OF DIFUNCTIONAL COMPOUNDS 445
AUTHOR INDEX 629
V

PREFACE
Since th e origina l volum e i n thi s serie s b y Ia n an d Shuye n Harrison , th e
goal o f th e Compendium of Organic Synthetic Methods ha s bee n t o facilitat e th e
search fo r functiona l grou p transformation s i n th e origina l literatur e o f organi c
chemistry. I n Volum e 2 , Afunctiona l compound s wer e added , an d thi s
compilation wa s continue d b y Loui s Hegedu s an d Lero y Wad e fo r Volum e 3 o f
the series . Professo r Wad e becam e th e autho r fo r Volum e 4 an d continue d wit h
Volume 5 . I bega n editin g th e serie s wit h Volum e 6 , wher e I introduce d a n
author inde x fo r th e firs t tim e an d adde d a ne w chapte r (Chapte r1 5 , Oxides) .
Volume 7 introduce d Sectio n 37 8 (Oxides-Alkynes ) throug h Sectio n 39 0
(Oxides-Oxides) . Th e Compendium i s a hand y deskto p referenc e tha t remain s a
valuable too l t o th e workin g organi c chemist , allowin g a quic k chec k o f th e
literature. Eve n i n th e er a o f powerfu l compute r searching , th e Compendium
allows on e t o "browse " fo r ne w reaction s an d transformation s tha t ma y b e o f
interest i n a rapi d an d logica l manner . Th e bod y o f organi c chemistr y literatur e
is ver y larg e an d th e Compendium i s a focuse d an d highl y representativ e surve y
of th e literature , an d i s offere d in tha t context .
Compendium of Organic Synthetic Methods, Volume 13 contain s bot h
functional grou p transformation s an d carbon-carbo n bond-formin g reaction s
from th e literatur e appearin g i n th e year s 2005 , 2006 , 2007 , an d 2008 . Th e
classification scheme s use d fo r Volume s 6-1 2 hav e bee n continued .
Difunctional compound s appea r i n Chapte r1 6 . Th e experience d use r o f th e
Compendium wil l requir e n o specia l instruction s fo r th e us e o f Volum e1 3 . Th e
vii
viii Compendiumo f Organic Syntheti c Methods , Volum e1 3
has bee n continue d a s i n Volume s 6-12 .
Every effor t ha s bee n mad e t o kee p th e manuscrip t error-free . Wher e ther e
are errors , I tak e ful l responsibility . I f ther e ar e question s o r comments , th e
reader i s encourage d t o contac t m e directl ya t th e address , phone , fax , o r emai l
given below .
As I hav e don e throughou t m y writin g career , I than k m y wife , Sarah , an d m y
son, Steven , fo r thei r encouragemen t an d suppor t durin g thi s work . I als o than k
Jonathan Ros e o f Wile y fo r his hel p i n th e publicatio n o f thi s volume .
Michael B . Smit h
Department o f Chemistry , Universit y o f Connecticu t
55 N . Eaglevill e Roa d
Storrs, Connecticu t 06269-306 0
Voice phone : [phone] Fax : [phone]
Email: [email protected] u
Storrs, Connecticu t
December, 201 3