Seven-Membered Heterocyclic Compounds Containing Oxygen and Sulfur

Name: Seven-Membered Heterocyclic Compounds Containing Oxygen and Sulfur
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Intro
THE CHEMISTRY OF HETEROCYCLIC COMPOUNDS A SERIES OF MONOGRAPHS
Preface
Contents
I. Oxepins and Reduced Oxepins
A. OXEPINS
1. Theoretical Interest
2. Preparation
3. Physical Properties
a. Infrared Absorption
b. Ultraviolet Absorption
c. Nuclear Magnetic Resonance
d. Thermodynamic Properties
4. Chemical Reactions
a. Addendum
B. DIHYDROOXEPINS
1. Introduction
2. Preparation
3. Physical Properties
a. Infrared Absorption
b. Ultraviolet Absorption
c. Nuclear Magnetic Resonance
4. Chemical Reactions
C. TETRAHYDROOXEPINS
1. Introduction
2. Preparation
3. Physical Properties
a. Infrared Absorption
b. Nuclear Magnetic Resonance
4. Chemical Reactions
D. HEXAHYDROOXEPINS (OXEPANS)
1. Preparation
a. Hexamethylene Oxide
b. Substituted Oxepans
(1) Ring Closure Reactions
(2) Ring Expansion Reactions
(3) Two-Component Reactions
2. Physical Properties of Hexamethylene Oxide
3. Chemical Reactions of Hexamethylene Oxide
4. Preparation and Reactions of Cyclic Acetals, Ketals, and Related Compounds
E. TABLES
F. REFERENCES
II. Oxepin Ring Systems Containing Two Rings
A. FUSED RINGS SYSTEMS
1. 2-Oxabicyclo[5.1.0]octanes
2. 2-Oxabicyclo[5.2.0]nonanes
3. 2H-Cyclopent[b]oxepins
4. 2H-Cyclopent[d]oxepins
5. Furo[3,4-b]oxepins
6. Furo[3,4-d]oxepins
7. 2H-Oxepino[2,3-b]pyrroles
8. Thieno[3,4-d]oxepins
9.1-Benzoxepins
a. Synthesis, Chemical Reactions, and Physical Properties of the Parent Compound
b. Synthesis and Chemical Reactions of Dihydro-l-benzoxepins
c. Synthesis and Chemical Reactions of Tetrahydro-l- benzoxepins
d. Synthesis and Chemical Reactions of Other Reduced 1-Benzoxepins
e. Physicochemical Properties of 2,3,4,5-Tetrahydro-1- benzoxepins
10.2-Benzoxepins
11. 3-Benzoxepins
B. SPIRANS
1. 1,7-Dioxaspiro[5.6]dodecanes
2. 1,4,6-Trioxaspiro[4.6]undecanes
C. BRIDGED SYSTEMS
1. 2-Oxabicyclo[3.2.2]nonanes
2. 3-Oxabicyclo[3.2.2]nonanes
3. 9-Oxabicyclo[3.3.2]decanes
4. 11-Oxabicyclo[4.4.1]undecanes
a. Partly or Fully Saturated Derivatives
b. 1,6-Oxido[10]annulenes
5. 3-Oxa-6,7-dithiabicyclo[3.2.2]nonanes
D. TABLES
E. REFERENCES
III. Oxepin Ring Systems Containing Three Rings
A. FUSED RING SYSTEMS
1. Cyclopenta[5.6]pyrano[4,3-b]oxepins
2. 8H-1,3-Dioxolo[4,5-h][3]benzoxepins
3. Dibenz[b,d]oxepins
4. Dibenz[b,e]oxepins
5. Dibenz[b,f]oxepins
6. Dibenz[c,e]oxepins
a. Dibenz[c,e]oxepin-5,7-diones (Diphenic Anhydrides)
(1) Synthesis
(2) Reactions
b. Dibenz[c,e]oxepin-5(7H)-ones
c. Dibenz[c,e]oxepins
(1) Synthesis
(2) Physical Properties
(3) Chemical Reactions
7. Naphth[ 1,2-b]oxepins
8. Naphth[l,2-c]oxepins
9. Naphth[2,1-b]oxepins
10. Naphth[2,3-b]oxepins
11. Naphth[2,3-d]oxepins
12. 1H-Naphth[ 1,8-cd]oxepins
13. [2]Benzoxepino[4,5-b]pyridines
14. 4H-Pyrano[ 3,2-h][1] benzoxepins
15. 6H-Oxepino[ 3,2-c][1,2]benzothiazines
16. 6H-Benzo[3,4]cyclohept[2,1-b]oxepins
B. BRIDGED AND SPIRAN RING SYSTEMS
1. Spiro[naphthalene-l(2H),4´-oxepanes]
2. 1,5-Ethano-3-benzoxepins
3. 5a,9a-[2]Buteno-3-benzoxepins
4. 15,16-Dioxatricyclo[8.4.1.13,8]hexadecanes
5. 3,6-Methano-1,4-benzodioxocins
6. 3,6-Methano-1,4-benzoxazocins
7. 2H-Spiro[1-benzoxepino-5,2´-dioxoles]
C. TABLES
D. REFERENCES
IV. Oxepin Ring Systems Containing More Than Three Rings
A. TETRACYCLIC SYSTEMS
1. Fused Ring Systems
a. 1H-Dibenzo[b,f]cyclopentoxepins
b. 4H-Fluoreno[4,5-cde]oxepins
c. 4H-Isobenzofuro[ 1,7-cd][2]benzoxepins
d. Benzofuro[3,2-c][1]benzoxepins
e. Benzo[d]dioxolo[4,5-h][2]benzoxepins
f. [1]Benzothieno[2,3-c][l]benzoxepins
g. 5H-Pyrido[2',3' : 5,6]oxepino[2,3-b]indoles
h. 4,9-Dioxa- 1,7-diazacyclohepta[def]fluorenes
i. Tribenz[b,d,f]oxepins
j. Benzo[c]naphth[2,1-e]oxepins
k. Benzo[c]naphth[2,3-e]oxepins
l. Benzo[e]naphth[ 1,2-b]oxepins
m. Benzo[e]naphth[2, l-bloxepins
n. Phenanthro[4,5-bcd]oxepins
o. Phenanthro[4,5-cde]oxepins
p. Phenanthro,[9,10-d]oxepins
q. [2]Benzopyrano[8,1-bc][1] benzoxepins
r. 1H-Benz[6,7]oxepino[2,3,4-ij]isoquinolines
s. Dibenz[2,3 : 6,7]oxepino[4,5-d]pyrimidines
t. [ 1]Benzoxepino[4,5-b]quinoxalines
u. [2]Benzoxepino[6,5,4-cde]cinnolines
v. 4H,6H-[2]Benzoxepino[6,5,4-def][2]benzoxepins
w. 4H,6H-[2]Benzothiepino[6,5,4-def][2]benzoxepins
x. 6H-[1]Benzoxepino[5,4-b][ 1,5]benzodiazepines
2. Bridged and Spiran Ring Systems
a. 4,4'(5H,5'H)-Spirobi[ 1-benzoxepins]
b. 9,10-Methanoxymethanoanthracenes
c. 10,9-(Epoxyethano)anthracenes
d. 4,6-Ethano(and etheno)dibenz[b,f]oxepins
B. PENTACYCLIC SYSTEMS
1. Fused Ring Systems
a. 14H-Dibenz[2,3 : 6,7]oxepino[4,5-b]indoles
b. Oxepino[3,4-b : 6,5-b']bisbenzofurans
c. Oxepino[4,5-b : 2,3-e']bisbenzofurans
d. Naphth[2', 1' : 6,7]oxepino[3,4-b]indolizines
e. Dinaphth[2,3-c : 2',3'-e]oxepins
f. Dinaphth[2,1-c: 1 ',2'-e]oxepins
g. Benzo[c]phenanthro[2,3-e]oxepins
h. Oxepino[3,4-b : 5,6-b']diquinolines
i. 2H-Benzo[8,9]phenanthro[4,5-bcd]oxepins
j. 7H, 15H- Bisoxepino [3', 4' : 4,5] pyrrolo[ 1,2-a: 1',2'- d]pyrazines
k. 2H, 10H-Oxepino[3,4-f: 5,6-f']bis[ 1,3]benzodioxoles
1. Dibenz[2,3 : 6,7]oxepino[4,5-b]quinoxalines
2. Bridged and Spiran Ring Systems
a. 4,6-(Methanoxymethoxy)cycloprop[f]isobenzofurans
b. 5-Oxapentacyclo[5.4.0.02.10.03.9.08.11]undecanes
C. HEXACYCLIC SYSTEMS
1. Acenaphtho[ 1,2-d]dibenz[b,f]oxepins
2. Piceno[6,7-cde]oxepins
3. 16H- Dibenzo[b,h][2]benzoxepino[3,4,5 - de][1,6]naphthyridines
4. Oxepino[3´,4´,5´,6´ : 4,5]phenanthro[9,10-b]quinoxalines
5. Spiro[dibenz[c,e]oxepin-5,9'-fluorenes]
6. Spiro[dibenz[c,e]oxepin-5,9'-xanthenes]
D. HEPTACYCLIC SYSTEMS
1. Difluoreno [1,2-c : 2', 1'-e]oxepins
2. Dianthra[l,2-c:2',1'-e]oxepins
3. Dianthra[9,1-bc: 1',9'-ef]oxepins
4. Dianthra[2,1-c: 1',2'-e]oxepins
5 . Diphenanthro[9,10-b : 9',10'-f]oxepins
6. Diphenanthro[9,10-c: 9',10'-e]oxepins
7. Benzo[6,7]perylo[ 1,12-cde]oxepins
8. 8H, 16H-7a,l5a-Epidithio-7H,15H-Bisoxepino[3',4':4,5]- pyrrolo[l,2-a: 1',2'-d]pyrazines
E. SYSTEMS CONTAINING MORE THAN SEVEN RINGS
1. Acenaphtho[ 1,2-d]dinaphth[2, l-b : 1 '2'-f]oxepins
2. Dinaphtho[2,1-e:2',1'-e]phenanthro[10,1-bc:9,8-b',c']bisoxepins
3. 5,20: 14,19-Bis(epoxymethano)-6,15-ethanonaphtho[2,3-c]- pentaphenes
F. REFERENCES
V. Dioxepins and Trioxepins
A. MONOCYCLIC DIOXEPINS
1. History, Structures, and Nomenclature
2. Methods of Preparation of 1,3-Dioxepins
a. Reaction of cis-2-Butene-1,4-dio1 with Aldehydes
b. Reaction of cis-2-Butene-1,4-diol with Ketones
c. Reaction of cis-2-Butene-1,4-diol with Acetals or Ketals
d. Reaction of cis-2-Butene-1,4-diol with an Aldehyde and an Acetal or Ketal
e. Reaction of cis-2-Butene-l,4-diol with a Ketone and an Acetal or Ketal
f. Reaction of cis-2-Butene-1,4-diol with Trialkyl Orthoformates
g. Dehydration of an Aldehyde 4-Hydroxy-2-buten- l-yl Hemiacetal
h. Reaction of cis-2-Butene-1,4-diol with Acetylenes
i. Reaction of cis-2-Butene-1,4-diol with Vinyl Ethers
j. Dehydrohalogenation of Halogenated 1,3-Dioxepanes
k. Miscellaneous Reactions
3. Types of 1,3-Dioxepins
a. Alkyl- and Aryl-Substituted 1,3-Dioxepins
b. Bis(1,3-dioxepins)
c. 2-Alkenyl- and 2-Alkadienyl-4,7-dihydro-1,3-dioxepins
d. 2-(Cyclohexen-1-yl)-4,7-dihydro-1,3-dioxepins
e. Spiro Derivatives
f. Halogenated 1,3-Dioxepins
g. x-(4,7-Dihydro-1,3-dioxepin-2-yl)phenols
h. Ether Derivatives
i. Keto-Substituted 1,3-Dioxepins
j. 2-Fury1 and 2-Pyranyl-4,7-dihydro-1,3-dioxepins
k. Esters of 4,7-Dihydro- 1,3-dioxepin-2-alkylcarboxylic Acids
l. Miscellaneous Derivatives
4. Identification of 1,3-Dioxepins
5. Reactions of 1,3-Dioxepins
a. Halogen Addition to the Double Bond
b. Hydrogenation of the Double Bond
c. Reactions with Acids
d. Diels-Alder Reactions
(1) Condensation with Cyclopentadienes
(2) 6,9-Methano-2,4-benzodioxepin Derivatives
e. Polymerizations
6. Physical Properties of 1,3-Dioxepins
B. CONDENSED DIOXEPINS
1. Benzodioxepins
a. Nomenclature and Structures
b. 2H-1,3-Benzodioxepins
c. 5H-1,4-Benzodioxepins
(1) Derivatives Found in Nature
(2) Methods of Preparation
(3) 5H-1,4-Benzodioxepin-(x)-ones
(4) 5H-1,4-Benzodioxepin-(x,y)-diones
(5) Physical Properties
d. 2H-1,5-Benzodioxepins
(1) Alkyl Derivatives
(2) Aldehydes
(3) Ketones
(4) Alcohols
(5) Halide Derivatives
(6) Amines
(7) Amides
(8) Esters
(9) Phenols
(10) Miscellaneous Derivatives
(11) 1,5-Benzodioxepin-3-ones
(12) Derivatives of 2H-1,5-Benzodioxepin-4-ones
(13) 1,5-Benzodioxepin-2,4-diones
(14) Physical Properties of 3,4-Dihydro-2H-1,5-benzodioxepins
e. 1 H-2,3-Benzodioxepins
(1) 1 H-2,3-Benzodioxepin Derivatives
(2) 1H-2,3-Benzodioxepin-1-o1 Derivatives
(3) 1,4-Epoxy-1 H-2,3-benzodioxepins
(4) 1,4-Epoxy-1 H-2,3-benzodioxepin-5-one Derivatives
(5) Physical Properties of 1 H-2,3-Benzodioxepins
f. 3H-2,4-Benzodioxepins
(1) Methods of Preparation
(2) Physical Properties
2. Dibenzodioxepins
a. History, Structures, and Nomenclature
b. Derivatives Found in Nature
c. Preparation of 11 H-Dibenzo[b,e][ 1,4]dioxepin
d. 11 H-Dibenzo[b,e][l,4]dioxepin-ll-ones
(1) Methods of Preparation
(2) Reactions
e. Preparation of 6H-Dibenzo[d,f][l,3]dioxepin Derivatives
f. Dibenzo[d,f][ 1,3]dioxepin-6-ones and Ketone Derivatives of 6H-Dibenzo[d, f][l,3]dioxepin
g. 6,6'-Spirobi(dibenzo[d,fl[l,3]dioxepin)
h. Physical Properties of Dibenzodioxepins
3. Naphthodioxepins
a. Nomenclature and Structures
b. Preparation
4. Dinaphthodioxepins
a. Nomenclature and Structures
b. Preparation
5. Other Dioxepin Systems Containing Two or More Rings
a. History, Types, Nomenclature, and Structures
b. 1,5-Dihydro-3H-[ 1,3]dioxepino[5,6-c]pyridines
c. 3.4-Dihydro-2H-[1,4]dioxepino[2,3-g]isoquinolines
d. Physical Properties
C. TRIOXEPINS
1. Types and Nomenclature
2. 2H,4H-1,3,5-Benzotrioxepins
3. 2,5-Epoxy-2H,4H- 1,3,4-benzotrioxepins
4. 2,5 : 8,l l-Diepoxybenzo[l,2-e:4,5-e']bis[l,2,4]trioxepins
5. 1,2,3-Trioxepins
6. 1,3,5-Trioxepins
D. TABLES
E. REFERENCES
VI. Terpene Oxepins
A. INTRODUCTION
B. e-LACTONES AND e-LACTOLS
1. Naturally Occurring e-Lactones
a. Structure
b. Derivatives and Ring A Reactions
c. Biogenesis
2. e-Lactones Originating by Peroxy Acid Oxidation
a. Classical Investigations
b. Examples
c. Special Aspects
3. Miscellaneously Derived e-Lactones and e-Lactols
C. ANHYDRIDES
D. MISCELLANEOUS OXEPINS
E. TABLES
F. REFERENCES
VII. Steroidal Oxepins
A. INTRODUCTION
B. NOMENCLATURE
C. RING A OXEPINS
D. RING B OXEPINS
E. RING C OXEPINS
F. TABLES
G. REFERENCES
VIII. Oxepins Derived from Sugars
A. INTRODUCTION
B. OXEPINS DERIVED FROM HEXOSES
1. 1,6-Anhydro-ß-D-allopyranoses
2. 1,6-Anhydro-ß-D-altropyranoses
3. 1,6-Anhydro-3-deoxy--ß-D-arabinohexopyranoses
4. 1,6-Anhydro-ß-D-galactopyranoses
5. 1,6-Anhydro-ß-D-galactofuranoses
6. 1,6-Anhydro-ß-D-glucopyranoses
a. Methods of Preparation
b. Proof of Structure
c. Reactions and Derivatives
d. Mechanism of Formation
e. Polymerization
7. 1,6-Anhydro-ß-D-glucofuranoses
8. 1,6-Anhydro-ß-D-gulopyranoses
9. 1,6-Anhydro-ß-D-idopyranoses
10. 1,6-Anhydro-ß-D-mannopyranoses
11. 1,6-Anhydro-3-deoxy-ß-D-ribohexopyranoses
12. 1,6-Anhydro-ß-D-talopyranoses
C. OXEPINS DERIVED FROM HEPTOSES
1. 2,7-Anhydro-ß-D-altroheptulopyranoses
2. 2,7-Anhydro-ß-D-altroheptulofuranoses
3. 2,7-Anhydro-a-L-galactoheptulopyranoses
4. 2,7-Anhydro-a-L-galactoheptulofuranoses
5. 2,7-Anhydro-ß-D-glucoheptulopyranoses
6. 1,6-Anhydro-D-gluco-ß-D-idoheptopyranose
7. 1,6-Anhydro-D-glycero-ß-D-guloheptopyranoses
8. 1,6-Anhydro-D-glycero-ß-D-idoheptopyranoses
9. 2,7-Anhydro-ß-L-guloheptulopyranoses
10. 2,7-Anhydro-ß-D-idoheptulopyranose
11. 2,7-Anhydro-ß-D-mannoheptulopyranoses
D. OXEPINS DERIVED FROM SUGARS AND ALDEHYDES
1. Formaldehyde Derivatives
2. Acetaldehyde and Higher Aldehyde Derivatives
E. OXEPINS RELATED TO SUGARS
F. REFERENCES
IX. Alkaloids Containing a Seven-Membered Oxygen Ring
A. INTRODUCTION
B. THE STRYCHNINE GROUP
1. General Background
2. Opening of the Oxepin Ring
3. Congeners of Strychnine
C. THE CULARINE GROUP
D. INSULARINE AND INSULANOLINE
E. REFERENCES
X. Monocyclic Seven-Membered Rings Containing Sulfur
A. INTRODUCTION
B. RINGS CONTAINING ONE SULFUR ATOM (THIEPINS AND DERIVATIVES)
1. Thiepins and Derivatives
2. Dihydrothiepins and Derivatives
3. Tetrahydrothiepins and Derivatives
4. Thiepanes
a. Occurrence
b. Preparation and Properties
c. Reactions
5. Thiepanones and Derivatives
a. 2-Thiepanones (e-Thiocaprolactones)
b. 3-Thiepanones
c. 4-Thiepanones
(1) Preparation
(2) Reactions
6. Thioseptanoses
C. RINGS CONTAINING TWO SULFUR ATOMS (DITHIEPINS AND DERIVATIVES)
1. 1,2-Dithiepins and Derivatives
a. Physical Properties
b. Preparation
c. Reactions
2. 1,3-Dithiepins and Derivatives
a. 1,3-Dithiepin
b. Dihydro-1,3-dithiepins
c. 1,3-Dithiepanes
(1) Physical Properties
(2) Preparation
3. 1,4-Dithiepins and Derivatives
a. 1 ,4-Dithiepin
b. Dihydro-1,4-dithiepins
c. 1,4-Dithiepanes
(1) 1 ,4-Dithiepane and Derivatives
(2) 1,4-Dithiepan-6-01 and Derivatives
(3) 1,4-Dithiepan-6-one and Derivatives
(a) Preparation
(b) Reactions
D. RINGS CONTAINING THREE SULFUR ATOMS (TRITHIEPINS AND DERIVA- TIVES)
1. 1,2,3-Trithiepins and Derivatives
2. 1,2,5-Trithiepins and Derivatives
a. Preparation and Structure
b. Stereochemistry
c. Reactions
d. Uses
3. 1,3,5-Trithiepins and Derivatives
E. RINGS CONTAINING FOUR OR MORE SULFUR ATOMS (TETRATHIEPINS, PENTATHIEPINS, HEXATHIEPINS, S7, AND DERIVATIVES)
1. Tetrathiepins and Derivatives
2. Pentathiepins and Derivatives
3. Hexathiepanes and S7
F. TABLES
G. REFERENCES
XI. Condensed Thiepins
A. INTRODUCTION
B. 2H-CYCLOPENTA[b]THIEPINS
C. 1 -BENZOTHIEPINS
1. 1-Benzothiepin and Derivatives
2. 1-Benzothiepin-1-oxide and Derivatives
3. 1-Benzothiepin-1,1-dioxide Derivatives
4. Dihydro-1-benzothiepin and Derivatives
5. 3,4-Dihydro-1-benzothiepin-5(2H)-one and Derivatives
6. 1-Benzothiepin-3,5(2H,4H)-dione and Derivatives
7. 2,3,4,5-Tetrahydro- 1-benzothiepin and Derivatives
8. 2,3,4,5-Tetrahydro- 1-benzothiepin-1, 1 -dioxide and Derivatives
D. 2-BENZOTHIEPINS
E. 3-BENZOTHIEPINS
1. 3-Benzothiepins and Derivatives
2. 3-Benzothiepin-3,3-dioxide and Derivatives
3. 1,2-Dihydro-3-benzothiepin-3,3-dioxide
4. 4,5-Dihydro-3-benzothiepin-l(2H)-one
5. 1,2,4,5-Tetrahydro-3-benzothiepin
F. NAPHTHOTHIEPINS
1. Naphtho[m,n-b]thiepins
2. Naphtho[m,n-d]thiepins
3. Naphtho[1,8-c,d]thiepins
G. DIBENZO[b,d]THIEPINS
H. DIBENZO[b,e]THIEPINS
1. Dibenzo[b,e]thiepin and Derivatives
2. Dibenzo[b,e]thiepin-11(6H)-one and Derivatives
3. 6,11-Dihydrodibenzo[b,e]thiepin and Derivatives
I. DIBENZO[b,f]THIEPINS
1. Dibenzo[b,f]thiepin and Derivatives
2. Dibenzo[b,f]thiepin-5-oxide and Derivatives
3. Dibenzo[b,f]thiepin-5,5-dioxide and Derivatives
4. Dibenzo[b,f]thiepin-10(11H)-one and Derivatives
5. 10,11-Dihydrodibenzo[b,f]thiepin and Derivatives
6. Hexahydro and Octahydrodibenzo[b,f]thiepins
J. DIBENZO[c,e]THIEPINS
K. BENZONAPHTHOTHIEPINS
L. TRIBENZO[b,d,f]THIEPINS
M. THIENOTHIEPINS AND BENZOTHIENOTHIEPINS
1. Thieno[3,2-c]thiepins and Derivatives
2. Thieno[2,3-d]thiepins and Derivatives
3. Thieno[3,4-c]thiepins and Derivatives
4. Thieno[3,4-d]thiepins and Derivatives
5. Benzo[e]thieno[2,3-b]thiepins and Derivatives
6. Benzo[ f]thieno[2,3-b]thiepins and Derivatives
N. FUROTHIEPINS
O. CYCLOALKADITHIEPINS
1. Cyclobutadithiepins. (3,5-Dithiabicyclo[5.2.0]nonanes)
2. Cyclopentadithiepins. (2,6-Dithiabicyclo[5.3.0]decane)
3. Cyclohexadithiepins. (2,6-Dithiabicyclo[5.4.0]undecane)
P. BENZODITHIEPINS
Q. DIBENZODITHIEPINS AND DINAPHTHODITHIEPINS
R. BENZOTRITHIEPINS
S. DINAPHTHOTRITHIEPINS
T. BENZOPENTATHIEPINS
U. PHYSIOLOGICAL ACTIVITY
V. BRIDGED SYSTEMS
1. x-Thiabicyclo[4.1.0]heptane Systems
2. x-Thiabicyclo[3,2.0]heptane Systems
3. x-Thiabicyclo[3.2.1]octane Systems
4. x-Thiabicyclo[4.2.1]nonane Systems
5. 2-Thiatricyclo[3.2.1.03,7]octane and Derivatives
6. 6-Thiatricyclo[3.2.1.13,8]nonane and Derivatives
W. TABLES
X. REFERENCES
INDEXES
Tables
I-1. Oxepins and Reduced Oxepins
II-1. Uv Data and Bromination Rate of 2,3,4,5-Tetrahydro-l-benzoxepins and Lower Ring Homologs
II-2. Solvolysis Kinetics of 7-Chloromethyl-2,3,4,5-tetrahydro-l- benzoxepin and Lower Ring Homologs
II-3. Uv Data and Bromination Rate of 2,3,4,5-Tetrahydro-l- benzoxepin-2-carboxylic Acid and Lower Ring Homologs
II-4. Uv Data and Molecular Geometry of 2,3,4,5-Tetrahydro-2-(N,N-dimethylamino)methyl-1-benzoxepin Methobromide and Lower Ring Homologs
II-5. l-Benzoxepins
II-6. 2-Benzoxepins
II-7. 3-Benzoxepins
III-1. Dibenz[b,e]oxepins
III-2. Dibenz[b,f]oxepins
III-3. Dibenz[c,e]oxepins
V-1. Reaction Products from Acetylenes and cis-2-Butene-l,4-diol
V-2. Reaction of cis-2-Butene-l,4-diol with Aldehydes
V-3. Reaction of cis-2-Butene-l,4-diol with an Acetal or Ketal and Concentrated Sulfuric Acid
V-4. Reaction of cis-2-Butene- 1,4-diol with Aldehydes and Acetals or Ketals in Benzene with Concentrated Sulfuric Acid
V-5. Reaction of cis-2-Butene-l,4-diol with Ketones and Acetals or Ketals in Benzene with Concentrated Sulfuric Acid
V-6. Reaction of cis-2-Butene-l,4-diol with Ketones in Benzene
V-7. Preparation of 2-Alkenyl and 2-Alkadienyl-4,7-dihydro-1,3- dioxepins by the Reaction of cis-2-Butene-l,4-diol with Unsaturated Acetals or Ketals, Unsaturated Aldehydes and Ketones
V-8. Reaction Products from cis-2-Butene-l,4-diol and Cyclic Ketones and Ketals
V-9. Reaction Products from cis-2-Butene-1,4-diol and Halo Acetals, Halo Aldehydes, or Halo Ketones and Acetals or Ketals
V-10. Reaction Products from cis-2-Butene-1,4-diol and Ring-Substituted Benzaldehydes
V-11. Reaction of cis-2-Butene-1,4-diol with a Trialkyl Orthoformate and Concentrated Sulfuric Acid
V-12. Reaction of cis-2-Butene-l,4-diol with an Alkoxy Acetal and an Acidic Catalyst
V-13. 6,9-Methano-2,4-Benzodioxepin Derivatives
V-14. Physical Properties of 1,3-Dioxepin
V-15. Physical Properties of 5-Substituted 1,3-Dioxepins
V-16. Physical Properties of 5H-1,4-Benzodioxepins
V-17. 2-Aminoalkyl-3,4-dihydro-2H-1,5-Benzodioxepins
V-18. 2-Guanidinoalkyl-2H-3,4-dihydro-l,5-Benzodioxepin Sulfates
V-19. 2-Guanidinoalkyl-3,4-Dihydro-2H-1,5-Benzodioxepins
V-20. Amide Derivatives of 3,4-Dihydro-2H- 1,5-Benzodioxepin
V-21. Physical Properties of 3,4-Dihydro-2H-1,5-Benzodioxepins
V-22. Physical Properties of 1H-2,3-Benzodioxepins
V-23. Physical Properties of 3H-2,4-Benzodioxepins
V-24. 11H-Dibenzo[b,e][1,4]dioxepin-11-ones
V-25. Physical Properties of Dibenzodioxepins
V-26. Physical Properties of Dioxepino Derivatives
V-27. 2,5-Epoxy-2H,4H-1,3,4-Benzotrioxepins
VI-1. Naturally Occurring Terpene Oxepins
VI-2. Products of Baeyer-Villiger Oxidation of Terpene Cyclo- hexanones
VI-3. Terpene Related Adipic Anhydrides
VII-1. Melting Points and Rotations for Most of the Compounds Discussed in the Chapter as Well as Certain Additional Selected Products
X-1. Uv Spectra of Amino-l,2-dithiepane Hydrochlorides
X-2. Reactivity of Cyclic Disulfides
X-3. Monocyclic Seven-Membered Rings Containing Sulfur
XI-1. Cyclopenta[b]thiepins
XI-2. 1 -Benzothiepins
XI-3. 2-Benzothiepins
XI-4. 3-Benzothiepins
XI-5. Naphthothiepins
XI-6. Dibenzo[b,d]thiepins
XI-7. Dibenzo[b,e]thiepins
XI-8. Dibenzo[b,f]thiepins
XI-9. Dibenzo[c,e]thiepins
XI-10. Benzonapthothiepins
XI-11. Tribenzo[b,d,f] thiepins
XI-12. Thienothiepins
XI-13. Furothiepins
XI-14. Cyclopentadithiepins
XI-15. Benzodithiepins
XI-16. Benzotrithiepins
XI-17. Benzopentathiepins
XI-18. Bridged Systems

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