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{{about|1,3-dioxolane|the other dioxolane isomer|1,2-dioxolane}}
{{chembox {{chembox
|Verifiedfields = changed
⚫ | verifiedrevid = 402001155
|Watchedfields = changed
⚫ | Reference=<ref> at ]</ref>
⚫ |verifiedrevid = 444710218
⚫ | Name = Dioxolane
⚫ |Reference=<ref> at ]</ref>
⚫ | ImageFileL1 = 1,3-dioxolane-2D-skeletal.png
⚫ |Name = Dioxolane
⚫ | ImageFileR1 = 1,3-dioxolane-3D-balls.png
⚫ |ImageFileL1 = 1,3-dioxolane-2D-skeletal.png
| IUPACName = Dioxolane
⚫ |ImageFileR1 = 1,3-dioxolane-3D-balls.png
⚫ | OtherNames = 1,3-dioxolane, formal glycol<ref></ref>
|PIN = 1,3-Dioxolane<ref>{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = ] | date = 2014 | location = Cambridge | page = 145 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4| chapter = Front Matter }}</ref>
⚫ | Section1 = {{Chembox Identifiers
|SystematicName = 1,3-Dioxacyclopentane
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫ |OtherNames = Dioxolane <br /> 5-Crown-2 <br /> Formal glycol<ref></ref>
⚫ | ChemSpiderID = 121835
⚫ |Section1 = {{Chembox Identifiers
⚫ | PubChem = 138198
⚫ |ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫ | InChI = 1/C3H6O2/c1-2-4-5-3-1/h1-3H2
⚫ |ChemSpiderID = 12066
⚫ | InChIKey = SNQXJPARXFUULZ-UHFFFAOYAS
⚫ |PubChem = 12586
⚫ | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
⚫ |ChEBI_Ref = {{ebicite|correct|EBI}}
⚫ | StdInChI = 1S/C3H6O2/c1-2-4-5-3-1/h1-3H2
|ChEBI = 87597
⚫ | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| ChEMBL = 3187281
⚫ | StdInChIKey = SNQXJPARXFUULZ-UHFFFAOYSA-N
|EINECS = 211-463-5
⚫ | CASNo_Ref = {{cascite|correct|CAS}}
⚫ |InChI = 1/C3H6O2/c1-2-4-5-3-1/h1-3H2
⚫ | CASNo = 646-06-0
⚫ |InChIKey = SNQXJPARXFUULZ-UHFFFAOYAS
⚫ | SMILES = O1OCCC1
⚫ |StdInChI_Ref = {{stdinchicite|correct|chemspider}}
⚫ |StdInChI = 1S/C3H6O2/c1-2-4-5-3-1/h1-3H2
⚫ |StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
⚫ |StdInChIKey = SNQXJPARXFUULZ-UHFFFAOYSA-N
|CASNo_Ref = {{cascite|correct|CAS}}
⚫ |CASNo = 646-06-0
|UNII_Ref = {{fdacite|correct|FDA}}
|UNII = Y57RBG19JL
| UNNumber = 1166
⚫ |SMILES = O1CCOC1
}} }}
| Section2 = {{Chembox Properties |Section2 = {{Chembox Properties
| Formula = C<sub>3</sub>H<sub>6</sub>O<sub>2</sub> |Formula = C<sub>3</sub>H<sub>6</sub>O<sub>2</sub>
| MolarMass = 74.08 g/mol |MolarMass = 74.08 g/mol
| Density = 1.06 g/cm<sup>3</sup> |Density = 1.06 g/cm<sup>3</sup>
| MeltingPtC = -95 |MeltingPtC = -95
| BoilingPtC = 75}} |BoilingPtC = 75}}
|Section7 = {{Chembox Hazards
| GHS_ref=<ref>{{cite web |title=1,3-Dioxolane |url=https://pubchem.ncbi.nlm.nih.gov/compound/12586#section=Safety-and-Hazards |website=pubchem.ncbi.nlm.nih.gov |language=en}}</ref>
| GHSPictograms = {{GHS02}}
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|225}}
| PPhrases = {{P-phrases|210|233|240|241|242|243|280|303+361+353|370+378|403+235|501}}
}}
}} }}


'''Dioxolane''' is an ] ] with the ] (CH<sub>2</sub>)<sub>2</sub>O<sub>2</sub>CH<sub>2</sub>. It is related to ] by interchange of one oxygen for a CH<sub>2</sub> group. The corresponding saturated 6-membered C<sub>4</sub>O<sub>2</sub> rings are called ]s. The ]ic 1,2-dioxolane (wherein the two oxygen centers are adjacent) is an ]. 1,3-Dioxolane is used as a ] and as a co] in ]s. '''Dioxolane''' is a ] ] with the ] (CH<sub>2</sub>)<sub>2</sub>O<sub>2</sub>CH<sub>2</sub>. It is related to ] (THF) by replacement of the ] (CH<sub>2</sub>) at the 2-position with an oxygen atom. The corresponding saturated 6-membered C<sub>4</sub>O<sub>2</sub> rings are called ]s. The ]ic 1,2-dioxolane (wherein the two oxygen centers are adjacent) is a ]. 1,3-dioxolane is used as a ] and as a co] in ]s.


==Dioxolanes as a class of compounds== ==As a class of compounds==
'''Dioxolanes''' are a group of ]s containing the dioxolane ring. Dioxolanes can be prepared by ] of ]s and ] of ]s with ].<ref>{{OrgSynth '''Dioxolanes''' are a group of ]s containing the dioxolane ring. Dioxolanes can be prepared by ] of ]s and ] of ]s with ].<ref>{{OrgSynth
|author=R. A. Daignault, E. L. Eliel |author=R. A. Daignault, E. L. Eliel
|year=1973 |year=1973
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|collvol=5 |collvol=5
|collvolpages=303 |collvolpages=303
|prep=CV5P0303}}</ref>
⚫ |prep=CV5P0303}}</ref> (+)-''cis''-Dioxolane is the ] for <small>L</small>-(+)-''cis''-2-methyl-4-trimethylammoniummethyl-1,3-dioxolane iodide which is a ] ].

]

⚫ (+)-''cis''-Dioxolane is the ] for {{chem name|<small>L</small>-(+)-''cis''-2-methyl-4-trimethylammoniummethyl-1,3-dioxolane iodide}} which is a ] ].

==Protecting groups==
Organic compounds containing ]s sometimes need ] so that they do not undergo reactions during transformations of other ]s that may be present. A variety of approaches to protection and deprotection of carbonyls<ref name = Greene /> including as dioxolanes<ref name = Greene2>{{cite book|chapter = 1,3-Dioxanes, 1,3-Dioxolanes|first1 = Theodora W.|last1 = Greene|first2 = Peter G. M.|last2 = Wuts|title = Greene's Protective Groups in Organic Synthesis|edition = 3rd|publisher = ]|year = 1999|pages = 308–322, 724–727|url = https://www.organic-chemistry.org/protectivegroups/carbonyl/dioxanes-dioxolanes.htm|access-date = June 20, 2017|isbn = 9780471160199|archive-date = December 7, 2016|url-status = live|archive-url = https://web.archive.org/web/20161207144346/http://www.organic-chemistry.org/protectivegroups/carbonyl/dioxanes-dioxolanes.htm}}</ref> are known. For example, consider the compound methyl cyclohexanone-4-carboxylate, where ] reduction will produce 4-hydroxymethylcyclohexanol. The ester functional group can be reduced without affecting the ] by protecting the ketone as a ]. The ketal is produced by acid catalysed reaction with ], the reduction reaction carried out, and the protecting group removed by hydrolysis to produce 4-hydroxymethylcyclohexanone.

]

] can also be used for deprotection of acetal or ketal-protected carbonyl compounds.<ref name = Greene>{{cite book|chapter = Dimethyl acetals|first1 = Theodora W.|last1 = Greene|first2 = Peter G. M.|last2 = Wuts|title = Greene's Protective Groups in Organic Synthesis|edition = 3rd|publisher = ]|year = 1999|pages = 297–304, 724–727|url = https://www.organic-chemistry.org/protectivegroups/carbonyl/dimethylacetals.htm|access-date = June 20, 2017|isbn = 9780471160199|archive-date = December 3, 2016|url-status = live|archive-url = https://web.archive.org/web/20161203200424/http://www.organic-chemistry.org/protectivegroups/carbonyl/dimethylacetals.htm}}</ref><ref name = Greene2 /> For example, deprotection of 2-phenyl-1,3-dioxolane to ] can be achieved in water in five minutes at 30&nbsp;°C.<ref>{{cite journal|title = Deprotection of Acetals and Ketals in a Colloidal Suspension Generated by Sodium Tetrakis(3,5-trifluoromethylphenyl)borate in Water|first1 = Chih-Ching|last1 = Chang|first2 = Bei-Sih|last2 = Liao|first3 = Shiuh-Tzung|last3 = Liu|journal = ]|year = 2007|volume = 2007|issue = 2|pages = 283–287|doi = 10.1055/s-2007-968009}}</ref>

::PhCH(OCH<sub>2</sub>)<sub>2</sub> &nbsp; + &nbsp; ] &nbsp; <chem>-></chem>&nbsp;PhCHO&nbsp;+&nbsp;]

==Natural products==
] is a ] that includes a 1,3-dioxolane ], and is an isomer of ] which has a 1,3-dioxane ring.<ref name = NatProd>{{cite book|chapter-url = https://books.google.com/books?id=OjO78KV6USAC&pg=PA222|chapter = 10. Neosporol, Sporol|pages = 222–224|series = The Total Synthesis of Natural Products|volume = 11|title = Part B: Bicyclic and Tricyclic Sesquiterpenes|editor1-first = Michael C.|editor1-last = Pirrung|editor2-first = Andrew T.|editor2-last = Morehead|editor3-first = Bruce G.|editor3-last = Young|publisher = ]|year = 2000|isbn = 9780470129630}}</ref> The ] of both compounds has been reported, and each includes a step in which a dioxolane system is formed using ] (TFPAA), prepared by the ] method.<ref name = UHP>{{cite journal|last1 = Ziegler|first1 = Fredrick E.|last2 = Metcalf|first2 = Chester A.|last3 = Nangia|first3 = Ashwini|last4 = Schulte|first4 = Gayle|title = Structure and total synthesis of sporol and neosporol|journal = ]|year = 1993|volume = 115|issue = 7|pages = 2581–2589|doi = 10.1021/ja00060a006}}</ref><ref name = eEROS2012>{{cite encyclopedia|doi = 10.1002/047084289X.rt254.pub2|encyclopedia = ]|title = Trifluoroperacetic Acid|first1 = Kenneth C.|last1 = Caster|first2 = A. Somasekar|last2 = Rao|first3 = H. Rama|last3 = Mohan|first4 = Nicholas A.|last4 = McGrath|first5 = Matthew|last5 = Brichacek|year = 2012|isbn = 978-0471936237}}</ref> This method involves no water, so it gives a completely ] peracid,<ref>{{cite journal|title = Oxidation Reactions Using Urea–Hydrogen Peroxide; A Safe Alternative to Anhydrous Hydrogen Peroxide|journal = ]|year = 1990|volume = 1990|issue = 9|pages = 533–535|doi = 10.1055/s-1990-21156|first1 = Mark S.|last1 = Cooper|first2 = Harry|last2 = Heaney|author-link2 = Harry Heaney|first3 = Amanda J.|last3 = Newbold|first4 = William R.|last4 = Sanderson}}</ref> necessary in this case as the presence of water would lead to unwanted ]s.<ref name = UHP />

:] &nbsp; + &nbsp; ] &nbsp; → &nbsp; ] &nbsp; + &nbsp; ] &nbsp; + &nbsp; ]

In the case of neosporol, a ]<ref>{{cite book|chapter = Prilezhaev reaction|pages = 274–281|last = Hagen|first = Timothy J.|chapter-url = https://books.google.com/books?id=WZ0DxnPNAdAC&pg=PA274|title = Name Reactions of Functional Group Transformations|editor1-first = Jie Jack|editor1-last = Li|editor2-first = E. J.|editor2-last = Corey|editor2-link = Elias James Corey|publisher = ]|year = 2007|isbn = 9780470176504}}</ref> with trifluoroperacetic acid is used to convert a suitable ] precursor to an ], which then undergoes a ring-expansion reaction with a proximate ] functional group to form the dioxolane ring.<ref name = UHP /><ref name = eEROS2012 />

]

A similar approach is used in the total synthesis of sporol, with the dioxolane ring later expanded to a dioxane system.<ref name = NatProd />


==See also== ==See also==
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{{Muscarinic acetylcholine receptor modulators}}


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