15501-33-4

Basic information

• Product Name: Neopentyl iodide
• Synonyms: 2,2-DIMETHYL-1-IODOPROPANE;1-IODO-2,2-DIMETHYLPROPANE;NEOPENTYL IODIDE;1-iodo-2,2-dimethyl-propan;2,2-Dimethylpropyl iodide;Propane,1-iodo-2,2-dimethyl-;Neopentyliodide, stabilized;2,2-Dimethyl-1-iodopropane, Neopentyl iodide
• CAS NO: 15501-33-4
• Molecular Formula: C₅H₁₁I
• Molecular Weight: 198.05
• EINECS: 239-533-0
• Mol File: 15501-33-4.mol
• Article Data: 11

Chemical Properties

• Melting Point: -85.6°C (estimate)
• Boiling Point: 70-71 °C100 mm Hg(lit.)
• Flash Point: 91 °F
• Appearance: colourless to light red liquid
• Density: 1.494 g/mL at 25 °C(lit.)
• Vapor Pressure: 14.2mmHg at 25°C
• Refractive Index: n20/D 1.489(lit.)
• Storage Temp.: Flammables area
• Stability: Stable, but may discolour upon exposure to light. Flammable. Incompatible with strong oxidizing agents.
• BRN: 1718796
• CAS DataBase Reference: Neopentyl iodide(CAS DataBase Reference)
• NIST Chemistry Reference: Neopentyl iodide(15501-33-4)
• EPA Substance Registry System: Neopentyl iodide(15501-33-4)

Safety Data

• Hazard Codes: Xi
• Statements: 10-36/37/38
• Safety Statements: 26-36
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• F: 8-9
• HazardClass: 3.2
• PackingGroup: III
• Hazardous Substances Data: 15501-33-4(Hazardous Substances Data)

Usage

Description

Neopentyl iodide, also known as 1-Iodo-2,2-dimethylpropane, is a colorless to light red liquid that is synthesized through the coupling mechanism facilitated by an electrochemically generated nickel(0) complex promoter [Ni(PPh3)4]. It is a versatile compound with various applications across different industries due to its unique chemical properties.

Uses

Used in Chemical Synthesis:
Neopentyl iodide is used as a reagent in the chemical synthesis industry for the production of various organic compounds. Its ability to undergo a range of reactions, such as substitution and elimination, makes it a valuable building block for creating complex molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, neopentyl iodide is used as an intermediate in the synthesis of drugs and active pharmaceutical ingredients. Its unique structure and reactivity allow for the development of novel therapeutic agents with potential applications in treating various medical conditions.
Used in Polymer Industry:
Neopentyl iodide is employed as a monomer in the polymer industry for the production of specialty polymers with specific properties. These polymers can be used in various applications, such as coatings, adhesives, and elastomers, where their unique characteristics are advantageous.
Used in Analytical Chemistry:
In analytical chemistry, neopentyl iodide can be used as a reference compound for the calibration of analytical instruments and methods. Its distinct chemical properties make it suitable for validating the performance of chromatography, spectroscopy, and other analytical techniques.
Used in Research and Development:
Neopentyl iodide is utilized as a research compound in academic and industrial research settings. Its unique reactivity and properties make it an interesting subject for studying various chemical reactions and exploring new synthetic pathways.

Synthesis Reference(s)

Journal of the American Chemical Society, 100, p. 1637, 1978 DOI: 10.1021/ja00473a069Organic Syntheses, Coll. Vol. 6, p. 830, 1988

InChI:InChI=1/C5H11I/c1-5(2,3)4-6/h4H2,1-3H3

Synthetic route

2,2-dimethyl-propanol-1 (75-84-3) → neopentyl iodide (15501-33-4)

Conditions	Yield
With 1-iodo-N,N,2-trimethylprop-1-en-1-amine In dichloromethane for 12h; Reflux; Inert atmosphere;	74%
With phosphorus; iodine
With pyridine; hydrogen fluoride; potassium iodide

2-dimethylamino-ethanesulfonic acid 2,2-dimethyl-propyl ester; hydriodide (66143-46-2) → neopentyl iodide (15501-33-4)

Conditions	Yield
In water; N,N-dimethyl-formamide at 120 - 130℃; for 2h;	68%
In N,N-dimethyl-formamide

neopentyl 2-(dimethylamino)ethanesulfonate (75391-29-6) → neopentyl iodide (15501-33-4)

Conditions	Yield
With hydrogen iodide In water; N,N-dimethyl-formamide at 120 - 130℃; for 2.5h;	68%

1-(2,2-dimethyl-propyl)-2,4-diphenyl-5,6-dihydro-benzo[h]quinolinium; iodide (87445-01-0) → neopentyl iodide (15501-33-4)

Conditions	Yield
at 230 - 240℃; under 0.3 - 0.8 Torr;	66%

2-<(2,2-dimethylpropoxy)sulfonyl>-N,N,N-trimethylethanaminium iodide (83634-79-1) → neopentyl iodide (15501-33-4)

Conditions	Yield
In N,N-dimethyl-formamide at 110℃; for 2h;	50%

2,2-dimethylpropane (463-82-1) → neopentyl iodide (15501-33-4)

Conditions	Yield
With tert-butylhypochlorite; mercury(II) iodide In 1,1,2-Trichloro-1,2,2-trifluoroethane at 47℃; for 8h; Irradiation;	28%
With tert-Butyl hypoiodite In tetrachloromethane

neopentyl tosylate (2346-07-8) → neopentyl iodide (15501-33-4)

Conditions	Yield
With sodium iodide
With potassium iodide In N,N-dimethyl-formamide at 99.9℃; for 8h;
With potassium iodide In N,N-dimethyl-formamide

2,2-dimethylpropylmagnesium chloride (13132-23-5) → neopentyl iodide (15501-33-4)

Conditions	Yield
With diethyl ether; iodine

2,2-dimethyl-propanol-1 (75-84-3) + methyl iodide (74-88-4) → neopentyl iodide (15501-33-4)

Conditions	Yield
With triphenyl phosphite

phosphonic acid bis-(2,2-dimethyl-propyl) ester (54722-84-8) → neopentyl iodide (15501-33-4)

Conditions	Yield
With hydrogen iodide

2,2-dimethylpropyl bromide (630-17-1) → neopentyl iodide (15501-33-4) + 2-iodo-2-methylbutane (594-38-7)

Conditions	Yield
With hydrogen iodide; cetyltributylphosphonium bromide at 105℃; for 60h;	A 73 % Spectr. B 14 % Spectr.

1,1-Diiodo-2,2-dimethylpropane (2443-89-2) → 2-methyl-but-2-ene (513-35-9) + neopentyl iodide (15501-33-4)

Conditions	Yield
In 1,2-dichloro-ethane; cyclohexene for 20h; Irradiation;	A 61 % Chromat. B 7 % Chromat.
In 1,2-dichloro-ethane; cyclohexene for 20h; Product distribution; Irradiation; variation of solvent and time;	A 61 % Chromat. B 7 % Chromat.
With sodium hydrogencarbonate; sodium thiosulfate In 1,2-dichloro-ethane for 31h; Product distribution; Irradiation;	A 65 % Chromat. B n/a

1,1-Diiodo-2,2-dimethylpropane (2443-89-2) → neopentyl iodide (15501-33-4)

Conditions	Yield
In cyclohexene for 4h; Irradiation;	32 % Chromat.

Imidazole-1-sulfonic acid 2,2-dimethyl-propyl ester (80667-83-0) → neopentyl iodide (15501-33-4)

Conditions	Yield
With tetra-(n-butyl)ammonium iodide In N,N,N,N,N,N-hexamethylphosphoric triamide Ambient temperature;

iodo-neopentoxyphosphonium salt (74745-83-8) → neopentyl iodide (15501-33-4)

2-(neopentyloxy)benzo-1,3,2-dioxaphosphole (65007-83-2) → neopentyl iodide (15501-33-4) + 2-iodo-2-methylbutane (594-38-7) + 2-Iodo-benzo[1,3,2]dioxaphosphole 2-oxide (74746-01-3)

hydrogen iodide (10034-85-2) + 2,2-Dimethyl-1,3-propanediol (126-30-7) → neopentyl iodide (15501-33-4) + 3-iodo-2,2-dimethyl-1-propanol (51916-34-8)

Conditions	Yield
at 100℃;

2,2-dimethyl-propan-1-ol → neopentyl iodide (15501-33-4)

Conditions	Yield
With hydrogen iodide

dimethyltrimethylene glycol → neopentyl iodide (15501-33-4)

Conditions	Yield
With hydrogen iodide at 100 - 110℃;

neopentylmercury chloride → neopentyl iodide (15501-33-4)

Conditions	Yield
With water; iodine; potassium iodide

water (7732-18-5) + iodine (7553-56-2) + chloro(2,2-dimethylpropyl)mercury (10284-47-6) + KI → neopentyl iodide (15501-33-4)

2,2-dimethylpropylamine (5813-64-9) → neopentyl iodide (15501-33-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) triethylamine, 2.) glacial acetic acid / 1.) methylene chloride, 25 deg C, 8 h, 2.) 6 h, 3.) water 2: 66 percent / 230 - 240 °C / 0.3 - 0.8 Torr View Scheme

2,2-dimethyl-propanol-1 (75-84-3) → neopentyl iodide (15501-33-4) + lithium chloride

Conditions	Yield
Multi-step reaction with 2 steps 1: PBr3 2: HI View Scheme
Multi-step reaction with 2 steps 2: dimethylformamide View Scheme

4-nitro-1H-pyrazole (2075-46-9) + neopentyl iodide (15501-33-4) → 1-neopentyl-4-nitro-1H-pyrazole

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 48h;	99%

neopentyl iodide (15501-33-4) → C5H11N(15)N2

Conditions	Yield
With hexadecyltributylphosphonium (1,3-15N2)-azide	97%

neopentyl iodide (15501-33-4) + hydroquinone (123-31-9) → 1,4-Bis(2,2-dimethylpropoxy)benzol (125520-67-4)

Conditions	Yield
With CsCO3 In diethylene glycol dimethyl ether at 150 - 160℃; for 72h; other hydroquinones, also phenol and hydroquinone diacetates;	96%
With CsCO3 In diethylene glycol dimethyl ether at 150 - 160℃; for 72h; reduced pressure;	96%
With potassium carbonate In N,N-dimethyl-formamide at 120℃; Sealed tube;	70%

neopentyl iodide (15501-33-4) + thiophenol (108-98-5) → neopentyl phenyl sulphide (7210-80-2)

Conditions	Yield
With potassium tert-butylate In dimethyl sulfoxide for 1h; Inert atmosphere; Irradiation;	96%

styrene (292638-84-7) + neopentyl iodide (15501-33-4) + sodium acetate (127-09-3) → (S)-4,4-dimethyl-1-phenylpentyl acetate

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In ethanol at 20 - 25℃; for 10h; Irradiation;	96%

neopentyl iodide (15501-33-4) + triptycene-1,4-diol (5969-70-0) → 9,10-Dihydro-1,4-bis(2,2-dimethylpropoxy)-9,10<1',2'>benzenoanthracen (125540-51-4)

Conditions	Yield
With CsCO3 In diethylene glycol dimethyl ether at 150 - 160℃; for 70h; reduced pressure;	95%

neopentyl iodide (15501-33-4) + diphenyl diselenide (1666-13-3) → 2,2-dimethyl-1-propyl phenyl selenide (96503-15-0)

Conditions	Yield
With dipotassium hydrogenphosphate; zinc In water; acetonitrile for 1h;	95%

neopentyl iodide (15501-33-4) + benzhydrylidene-benzyl-amine (7699-79-8) → N-(diphenylmethylene)-3,3-dimethyl-1-phenylbutan-1-amine

Conditions	Yield
With sodium hexamethyldisilazane In tert-butyl methyl ether at 23℃; for 2h; Reagent/catalyst; Solvent; Concentration; Inert atmosphere; Glovebox;	95%

neopentyl iodide (15501-33-4) + phenol (108-95-2) → 1-phenoxy-2,2-dimethylpropane (2189-88-0)

Conditions	Yield
With CsCO3 In diethylene glycol dimethyl ether at 150 - 160℃; for 12h; reduced pressure;	94%

neopentyl iodide (15501-33-4) + ethyl vinyl sulfone (1889-59-4) → ethyl 4,4-dimethylpentyl sulfone

Conditions	Yield
With copper(l) iodide; zinc In N,N-dimethyl-formamide at 0 - 20℃;	94%

neopentyl iodide (15501-33-4) → 2,2,5,5-tetramethylhexane (1071-81-4) + 2,2-dimethylpropane (463-82-1) + 1,1-dimethylcyclopropane (1630-94-0)

Conditions	Yield
With tetrabutylammonium perchlorate; nickel(II) perchlorate; triphenylphosphine In acetonitrile at 25℃;	A 92% B 2.5% C 2.5%

neopentyl iodide (15501-33-4) + acetophenone (98-86-2) → 4,4-dimethyl-1-phenylpentan-1-one (37608-93-8)

Conditions	Yield
With potassium tert-butylate; iron(II) bromide In dimethyl sulfoxide at 60℃; for 0.666667h;	92%
With potassium tert-butylate In dimethyl sulfoxide for 4h; Irradiation;	65 % Chromat.

neopentyl iodide (15501-33-4) + trimethylstannyl sodium (16643-09-7) → (neopentyl)trimethylstannane (55204-72-3)

Conditions	Yield
In tetrahydrofuran 0°C in N2-atmosphere; various yields for various conditions;	92%

neopentyl iodide (15501-33-4) + 4-tert-butyl-5-(2'-hydroxy-2-methoxy-1,1'-binaphthyl-7-yl)-3,3-dimethyl-2,3-dihydrofuran → C36H42O3

Conditions	Yield
Stage #1: 4-tert-butyl-5-(2'-hydroxy-2-methoxy-1,1'-binaphthyl-7-yl)-3,3-dimethyl-2,3-dihydrofuran With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 0.5h; Inert atmosphere; Stage #2: neopentyl iodide In N,N-dimethyl-formamide for 2h; Inert atmosphere; Reflux;	92%

neopentyl iodide (15501-33-4) + 1-neopentyl-1H-1,3-benzazaphosphole (1039451-34-7) → 1,3-bis(2,2-dimethylpropyl)-1,3-benzazaphospholine 3-oxide

Conditions	Yield
With copper(l) iodide; water; cesium acetate In N,N-dimethyl-formamide at 125℃; under 0.750075 Torr; for 18h; Schlenk technique; Inert atmosphere;	92%

neopentyl iodide (15501-33-4) + N-ethylidenecyclohexylamine (113832-57-8, 1193-93-7) + 4-t-butoxy-3-methyl-2,5-difluoropyridine (169749-84-2) → 2-(4-tert-Butoxy-5-fluoro-3-methyl-pyridin-2-yl)-4,4-dimethyl-pentanal

Conditions	Yield
With lithium diisopropyl amide at 0 - 25℃;	91%

neopentyl iodide (15501-33-4) + {difluoro{N,N'-bis(3-pentanon-2-ylidene)-1,3-diaminopropanedioximato}borato}rhodium (53335-25-4) → (neopentyl)iodo{difluoro{2,2'-{1,3-propanediylbis(nitrilo)}bis{3-pentanone oximato}}borato}rhodium(III) (99355-17-6)

Conditions	Yield
In tetrahydrofuran Kinetics; under N2, in the dark, Rh(I) reagent and 1.5 equiv. of t-BuCH2I refluxed in THF for 1 h / kinetics measured at 30.5+-2°C; recrystd. from CH2Cl2/EtOH; elem. anal.;	91%
In [D3]acetonitrile Kinetics; under N2, in the dark, Rh(I) reagent and t-BuCH2I reacted in CD3CN at 28.5°C; monitored by NMR;

neopentyl iodide (15501-33-4) + chloro-p-hydroquinone (615-67-8) → 2-Chlor-1,4-bis(2,2-dimethylpropoxy)benzol (125520-68-5)

Conditions	Yield
With CsCO3 In diethylene glycol dimethyl ether at 150 - 160℃; for 18h; reduced pressure;	90%

neopentyl iodide (15501-33-4) + C17H31P2(1+)*I(1-) → C22H42P2

Conditions	Yield
Stage #1: neopentyl iodide With tert.-butyl lithium In diethyl ether; pentane at 20℃; for 0.5h; Cooling; Stage #2: C17H31P2(1+)*I(1-) In diethyl ether; pentane at 20℃; for 1.5h;	90%

1H-indole-3-carboxylic acid (771-50-6) + neopentyl iodide (15501-33-4) → 1-(2,2-Dimethylpropyl)-1H-indole-3-carboxylic acid (739365-09-4)

Conditions	Yield
Stage #1: 1H-indole-3-carboxylic acid With sodium hydride In DMF (N,N-dimethyl-formamide) at 20℃; for 0.166667h; Stage #2: neopentyl iodide In DMF (N,N-dimethyl-formamide) at 80℃; for 15h;	89%

6-chloropyridine-3-ol (41288-96-4) + neopentyl iodide (15501-33-4) → 2-chloro-5-(2,2-dimethylpropoxy)pyridine (1154030-27-9)

Conditions	Yield
With caesium carbonate In diethylene glycol dimethyl ether at 160℃; for 4h; microwave irradiation;	88%
With caesium carbonate In diethylene glycol dimethyl ether at 160℃; for 4h; Microwave irradiation;	88%

di(pyridin-2-yl)amine (1202-34-2) + neopentyl iodide (15501-33-4) → N-(2,2-dimethylpropyl)-N-(2-pyridyl)pyridin-2-amine (1258543-20-2)

Conditions	Yield
Stage #1: di(pyridin-2-yl)amine With potassium hydroxide In dimethyl sulfoxide for 0.75h; Stage #2: neopentyl iodide In dimethyl sulfoxide at 20℃; for 20h;	88%

neopentyl iodide (15501-33-4) + 2-[N-methyl-N-(pyridin-2-yl)amino]pyridine (123368-97-8) → N-(2,2-dimethylpropyl)-N-(2-pyridyl)pyridin-2-amine (1258543-20-2)

Conditions	Yield
Stage #1: 2-[N-methyl-N-(pyridin-2-yl)amino]pyridine With potassium hydroxide In dimethyl sulfoxide for 0.75h; Schlenk technique; Inert atmosphere; Stage #2: neopentyl iodide In dimethyl sulfoxide at 25℃; for 20h; Schlenk technique; Inert atmosphere;	88%

neopentyl iodide (15501-33-4) + 3-methyl-1,3-diphenylcyclobutanol → 3,6,6-trimethyl-1,3-diphenylheptan-1-one (1432045-57-2)

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; caesium carbonate In toluene at 110℃; for 14h; Inert atmosphere;	87%

styrene (292638-84-7) + neopentyl iodide (15501-33-4) → 4,4-dimethyl-1-phenyl-1-pentene (40132-64-7)

Conditions	Yield
With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In benzene at 20℃; for 12h; Heck Reaction; Inert atmosphere; Glovebox; Irradiation; Sealed tube; Schlenk technique;	87%

neopentyl iodide (15501-33-4) + 3,4,8,9-tetramethyl-1,6-diphospha-bicyclo-[4.4.0]deca-3,8-diene (1258870-28-8) → C17H31P2(1+)*I(1-)

Conditions	Yield
In neat (no solvent) at 130℃; for 14h; Inert atmosphere; Glovebox;	87%

neopentyl iodide (15501-33-4) + phenylmagnesium bromide → (2,2-dimethyl-1-propyl)benzene (1007-26-7)

Conditions	Yield
[1,1'-bis(diphenylphosphino)ferrocene]nickel(II) chloride In diethyl ether Heating;	86%
[Li(tmeda)]2[Fe(C2H4)4] In tetrahydrofuran at 0℃;	74%

neopentyl iodide (15501-33-4) + 2-Naphthalenethiol (91-60-1) → 2-naphthyl neopentyl sulfide (1296204-18-6)

Conditions	Yield
With potassium tert-butylate In dimethyl sulfoxide for 1h; Inert atmosphere; Irradiation;	86%

neopentyl iodide (15501-33-4) + [hydroxy(tosyloxy)iodo]benzene (27126-76-7) → Toluene-4-sulfonic acid 1,1-dimethyl-propyl ester

Conditions	Yield
In dichloromethane for 3h; Ambient temperature;	85%

neopentyl iodide (15501-33-4) + 2-acetyl-1-methylpyrrole enolate ion → 1-(1-methyl-1H-pyrrole-2-yl)-4,4-dimethyl-pentanone

Conditions	Yield
With potassium tert-butylate In dimethyl sulfoxide at 40℃; for 3h; Substitution; Irradiation;	85%

Upstream product

• 75-84-3 2,2-dimethyl-propanol-1 
• 2346-07-8 neopentyl tosylate 
• 13132-23-5 2,2-dimethylpropylmagnesium chloride 
• 74-88-4 methyl iodide 
• 463-82-1 2,2-dimethylpropane 
• 54722-84-8 phosphonic acid bis-(2,2-dimethyl-propyl) ester 
• 66143-46-2 2-dimethylamino-ethanesulfonic acid 2,2-dimethyl-propyl ester; hydriodide 
• 630-17-1 2,2-dimethylpropyl bromide 
• 2443-89-2 1,1-Diiodo-2,2-dimethylpropane 
• 80667-83-0 Imidazole-1-sulfonic acid 2,2-dimethyl-propyl ester 
• 87445-01-0 1-(2,2-dimethyl-propyl)-2,4-diphenyl-5,6-dihydro-benzo[h]quinolinium; iodide 
• 74745-83-8 iodo-neopentoxyphosphonium salt 
• 65007-83-2 2-(neopentyloxy)benzo-1,3,2-dioxaphosphole 
• 83634-79-1 2-<(2,2-dimethylpropoxy)sulfonyl>-N,N,N-trimethylethanaminium iodide 

Downstream Products

• 463-82-1 2,2-dimethylpropane 
• 17348-57-1 1-ethoxy-2,2-dimethyl-propane 
• 594-36-5 2-methyl-2-butylchloride 
• 507-45-9 2,3-dichloro-2-methylbutane 
• 594-51-4 2,3-dibromo-2-methylbutane 
• 1071-81-4 2,2,5,5-tetramethylhexane 
• 3740-00-9 neopentyl(triphenyl)phosphonium iodide 
• 62016-49-3 2-methoxy-2-methylbutane 
• 122348-66-7 (R)-(+)-N-(2',2'-dimethylpropyl)-1-phenylethylamine 
• 1050-47-1 Methyltris(p-methoxyphenyl)phosphonium iodide 
• 107770-02-5 neopentyl-tris(p-methoxyphenyl)phosphonium iodide 
• 107770-03-6 [4-(2,2-Dimethyl-propoxy)-phenyl]-(2,2-dimethyl-propyl)-bis-(4-methoxy-phenyl)-phosphonium; iodide 
• 107770-04-7 Bis-[4-(2,2-dimethyl-propoxy)-phenyl]-(2,2-dimethyl-propyl)-(4-methoxy-phenyl)-phosphonium; iodide 
• 107770-06-9 [4-(2,2-Dimethyl-propoxy)-phenyl]-bis-(4-methoxy-phenyl)-methyl-phosphonium; iodide 

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The hydrogenolysis of neopentyl iodide on reduced Co or Pt dispersed on MgO support yields increasing amounts of 2-metylbutane and 2-methylbutenes in addition to neopentane, as the temperature is raised from 50 to 150°C. These results support the idea that a π-complexed half-reaction state is ...detailed

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The chemistry of neopentyl iodide on Pt(1 1 1) single-crystal surfaces was characterized by temperature programmed desorption and reflection-absorption infrared spectroscopy. As with many other halo hydrocarbons, the first thermal reaction observed with neopentyl iodide on the platinum surface i...detailed

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Relevant articles and documents

ON THE STRUCTURE OF tert-BUTYL HYPOIODITE.

A compound known as 'tert-butyl hypoiodite' has hitherto been referred to in the literature as a reagent with some synthetic utility. Three methods of preparation have been used to make this material: the reaction of tert-butyl hypochlorite with iodine, the reaction of tert-butyl hypochlorite with metal iodides, and the reaction of potassium tert-butoxide with iodine. Physical and chemical evidence is offered to show that the reagent obtained from the first of these methods is different from that made from the latter two methods. Reaction schemes are proposed to account for the different properties and reactivities of the two reagents. Structures are proposed for the two reagents which rationalize both the physical and chemical properties of the two materials.

Stereodynamics of Substituted Neopentanes

tert-Butyl rotation barriers have been measured in four monosubstituted neopentanes (Me3CCH2X, X=Me, Cl, Br, I) by using 270-MHz 1H dynamic NMR spectroscopy.The barrier depends on X in the order: Me Cl = ca.Br = ca.I.As a complement to the experimental DNMR data, Allinger's MM2 molecular mechanics program (1980 force field) was used to calculate optimized equilibrium geometries and tert-butyl rotation barriers for the four compounds.The MM2 barriers are compared to previously reported MM1 barriers.

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A transition-metal-free Heck-type reaction between alkenes and alkyl iodides enabled by light in water

A transition-metal-free coupling protocol between various alkenes and non-activated alkyl iodides has been developed by using photoenergy in water for the first time. Under UV irradiation and basic aqueous conditions, various alkenes efficiently couple with a wide range of non-activated alkyl iodides. A tentative mechanism, which involves an atom transfer radical addition process, for the coupling is proposed.

Finkelstein Reaction with Aqueous Hydrogen Halides Efficiently Catalysed by Lipophilic Quarternary Onium Salts

The rate of halogen metathesis between halogenoalkanes RX 1-4 (X = F, Cl, Br, I) and aqueous concentrated hydrogen halides HY (Y = Cl, Br, I) is strongly accelerated under phase-transfer catalysis conditions, without solvent.The amount and nature of the nucleophilic species in the organic phase were determined.