Journal of Organic Chemistry p. 5030 - 5034 (2015)
Update date:2022-07-29
Topics:
Kvaskoff, David
Becker, Jürgen
Wentrup, Curt
1-Azulenylcarbene 18 has been generated from 5-(1-azulenyl)tetrazole and the sodium salt of azulene-1-carbaldehyde tosylhydrazone using the falling solid flash vacuum pyrolysis (FS-FVP) method. The principal products, which are also formed from both 1- and 2-naphthylcarbenes, cyclobuta[de]naphthalene 6, cyclopenta[cd]indene 16, and benzofulvenallene 17, are explained in terms of two reaction paths, (a) a rearrangement to benzofulvenyl-7-carbene 13 and (b) a rearrangement to 1-naphthylcarbene 1. Moreover, 16 is also formed from 2-azulenylcarbene 30, thereby indicating the occurrence of a 2-azulenylcarbene-1-azulenylcarbene rearrangement. The reaction mechanisms are supported by density functional theory calculations at the B3LYP/6-31G?? level, which indicate that all the rearrangements have activation barriers of <35 kcal/mol, thus making them readily achievable under FVP conditions. Chemical Presented.
View MoreCHANGZHOU HANGYU PHARMACEUTICAL TECHNOLOGY CO., LTD
website:http://www.czyys.com
Contact:0086-519-88802789
Address:No.300,Yanling Middle Road, Changzhou, Jiangsu, China
Chengdu Green technology Co.,Ltd.
Contact:86-28-82608355
Address:C9 ,Economic Headquarters, Economic Development Zone, Chengdu.
Zhejiang Linhai Xinhua Chemicals Factory
Contact:0086-13661858911
Address:Xunqiao Development Zone, Linhai, Zhejiang, China
Golden Union Agrochemical Import and Export Co., Ltd.
Contact:86-755-23910527
Address:Room 1106, Tower 3A, Excellence Century Center, Futian District, Shenzhen, China
Tengzhou Runlong Fragrance Co., Ltd.
website:http://www.tzrunlong.com/
Contact:0086-15665710862
Address:No. 78, Fushan Road, Biomedical Industrial Park, Dawu Town, Tengzhou, Shandong, 277514 China
Doi:10.1021/ja00736a028
(1971)Doi:10.1016/j.bmcl.2015.12.104
(2016)Doi:10.1016/j.tetlet.2007.03.164
(2007)Doi:10.1002/jlcr.2590110405
(1975)Doi:10.1007/BF00906785
(1976)Doi:10.1016/S0040-4039(03)00826-8
(2003)