2-adamantyl tosylate

Base Information

• Chemical Name: 2-adamantyl tosylate
• CAS No.: 25139-43-9
• Molecular Formula: C₁₇H₂₂O₃S
• Molecular Weight: 306.426
• Mol file: 25139-43-9.mol

Synonyms:2-adamantyl tosylate

Chemical Property of 2-adamantyl tosylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-adamantyl tosylate

There total 15 articles about 2-adamantyl tosylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

2-adamantyl azoxytosylate (76030-76-7,81765-53-9,121334-86-9) → 2-adamantyl tosylate (25139-43-9)

Guidance literature:

In chloroform-d1; at 65 ℃; for 72h; EtOH, 60-62 deg C, 4 d;

DOI:10.1039/P29840001693

Reference yield: 82.0%

1-adamantanol (700-57-2) + p-toluenesulfonyl chloride (98-59-9) → 2-adamantyl tosylate (25139-43-9)

Guidance literature:

With pyridine; at 20 ℃;

DOI:10.1055/s-0032-1317473 DOI:10.1055/s-0032-1317473

Reference yield: 65.0%

ethanol (64-17-5) + 3-endo-<(tosyloxy)methyl>bicyclo<3.3.1>non-6-ene (30860-11-8) → 1-adamantanol (700-57-2) + 2-adamantyl tosylate (25139-43-9) + 1-azidoadamantane (34197-88-1) + 2-adamantyl ethyl ether (29542-65-2)

Guidance literature:

With sodium azide; at 20 ℃; for 5h; Title compound not separated from byproducts;

DOI:10.1021/ja00342a037

upstream raw materials:

ethanol

3-endo-<(tosyloxy)methyl>bicyclo<3.3.1>non-6-ene

acetic acid

2-adamantyl azoxytosylate

Downstream raw materials:

2-adamantyl bromide

2-chloroadamantane

2-Phenyladamantane

2-(phenylthio)tricyclo<3.3.1.1^3,7>decane

Refernces

• 1、 Maskill, H.,Thompson, John T.,Wilson, Alan A.. "Internal Return in the Solvolysis of Secondary Alkyl Arenesulphonates". . p. 1239 - 1240. Retrieved 1981.
• 2、 Liu, Yajun,Xu, Yongnan,Jung, Sun Ho,Chae, Junghyun. "A facile and green protocol for nucleophilic substitution reactions of sulfonate esters by recyclable ionic liquids [bmim][X]". supporting information. p. 2692 - 2698,7. Retrieved 2012/12/12.
• 3、 Spiniello, Marisa,White, Jonathan M.. "Low-temperature x-ray structural studies of the ester and ether derivatives of cis- and trans-4-tert-butyl cyclohexanol and 2-adamantanol: Application of the variable oxygen probe to determine the relative σ-donor ability of C-H and C-C bonds". . p. 3094 - 3101. Retrieved 2007/10/03.