NUCLEOPHILIC SUBSTITUTION REACTIONS OF NEOPENTYL AND NEOPHYL
IODIDES WITH 2-ARYL-1,3-DITHIANE ANIONS
Gabriela Oksdath Mansilla and Alicia B. Peñéñory
Instituto de Investigaciones en Físico Química de Córdoba (INFIQC), Depto Química Orgánica, Fac.
de Ciencias Químicas, UNC, Córdoba (5000), Argentina.
E-mail: penenory@fcq.unc.edu.ar
penenory@fcq.unc.edu.ar1,3-Dithiane anions are often used as acyl anion equivalents for C-C bond forming
reactions,1 which is a common and successful strategy for the construction of complex natural
products.2 These anions react with common electrophiles such as alkyl, allyl and benzyl halides,
aldehydes, ketones and carboxylic acid derivatives by polar mechanisms. Furthermore, the
participation of 2-lithio-1,3-dithiane as electron donor was suggested in the reaction with a
neopentyl-type radical probe 5,5-dimethyl-6-iodo-1-hexene, with formation of 6-11% of cyclized
alkylated product.3 These reactions were performed at very low temperature (-20°C) in THF or THFTMDA
as solvent, and a chain process was disregarded.
To further explore the possibility of dithiane anions as electron donors in a radical
nucleophilic substitution (SRN1),4 we have studied the reactions of 2-aryl-1,3-dithiane anions (1) with
neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1
neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1
neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1
as solvent, and a chain process was disregarded.
To further explore the possibility of dithiane anions as electron donors in a radical
nucleophilic substitution (SRN1),4 we have studied the reactions of 2-aryl-1,3-dithiane anions (1) with
neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1
neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1
neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1
as solvent, and a chain process was disregarded.
To further explore the possibility of dithiane anions as electron donors in a radical
nucleophilic substitution (SRN1),4 we have studied the reactions of 2-aryl-1,3-dithiane anions (1) with
neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1
neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1
neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1
aldehydes, ketones and carboxylic acid derivatives by polar mechanisms. Furthermore, the
participation of 2-lithio-1,3-dithiane as electron donor was suggested in the reaction with a
neopentyl-type radical probe 5,5-dimethyl-6-iodo-1-hexene, with formation of 6-11% of cyclized
alkylated product.3 These reactions were performed at very low temperature (-20°C) in THF or THFTMDA
as solvent, and a chain process was disregarded.
To further explore the possibility of dithiane anions as electron donors in a radical
nucleophilic substitution (SRN1),4 we have studied the reactions of 2-aryl-1,3-dithiane anions (1) with
neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1
neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1
neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1
as solvent, and a chain process was disregarded.
To further explore the possibility of dithiane anions as electron donors in a radical
nucleophilic substitution (SRN1),4 we have studied the reactions of 2-aryl-1,3-dithiane anions (1) with
neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1
neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1
neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1
as solvent, and a chain process was disregarded.
To further explore the possibility of dithiane anions as electron donors in a radical
nucleophilic substitution (SRN1),4 we have studied the reactions of 2-aryl-1,3-dithiane anions (1) with
neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1
neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1
neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1
aldehydes, ketones and carboxylic acid derivatives by polar mechanisms. Furthermore, the
participation of 2-lithio-1,3-dithiane as electron donor was suggested in the reaction with a
neopentyl-type radical probe 5,5-dimethyl-6-iodo-1-hexene, with formation of 6-11% of cyclized
alkylated product.3 These reactions were performed at very low temperature (-20°C) in THF or THFTMDA
as solvent, and a chain process was disregarded.
To further explore the possibility of dithiane anions as electron donors in a radical
nucleophilic substitution (SRN1),4 we have studied the reactions of 2-aryl-1,3-dithiane anions (1) with
neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1
neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1
neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1
as solvent, and a chain process was disregarded.
To further explore the possibility of dithiane anions as electron donors in a radical
nucleophilic substitution (SRN1),4 we have studied the reactions of 2-aryl-1,3-dithiane anions (1) with
neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1
neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1
neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1
as solvent, and a chain process was disregarded.
To further explore the possibility of dithiane anions as electron donors in a radical
nucleophilic substitution (SRN1),4 we have studied the reactions of 2-aryl-1,3-dithiane anions (1) with
neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1
neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1
neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1
products.2 These anions react with common electrophiles such as alkyl, allyl and benzyl halides,
aldehydes, ketones and carboxylic acid derivatives by polar mechanisms. Furthermore, the
participation of 2-lithio-1,3-dithiane as electron donor was suggested in the reaction with a
neopentyl-type radical probe 5,5-dimethyl-6-iodo-1-hexene, with formation of 6-11% of cyclized
alkylated product.3 These reactions were performed at very low temperature (-20°C) in THF or THFTMDA
as solvent, and a chain process was disregarded.
To further explore the possibility of dithiane anions as electron donors in a radical
nucleophilic substitution (SRN1),4 we have studied the reactions of 2-aryl-1,3-dithiane anions (1) with
neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1
neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1
neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1
as solvent, and a chain process was disregarded.
To further explore the possibility of dithiane anions as electron donors in a radical
nucleophilic substitution (SRN1),4 we have studied the reactions of 2-aryl-1,3-dithiane anions (1) with
neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1
neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1
neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1
as solvent, and a chain process was disregarded.
To further explore the possibility of dithiane anions as electron donors in a radical
nucleophilic substitution (SRN1),4 we have studied the reactions of 2-aryl-1,3-dithiane anions (1) with
neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1
neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1
neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1
aldehydes, ketones and carboxylic acid derivatives by polar mechanisms. Furthermore, the
participation of 2-lithio-1,3-dithiane as electron donor was suggested in the reaction with a
neopentyl-type radical probe 5,5-dimethyl-6-iodo-1-hexene, with formation of 6-11% of cyclized
alkylated product.3 These reactions were performed at very low temperature (-20°C) in THF or THFTMDA
as solvent, and a chain process was disregarded.
To further explore the possibility of dithiane anions as electron donors in a radical
nucleophilic substitution (SRN1),4 we have studied the reactions of 2-aryl-1,3-dithiane anions (1) with
neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1
neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1
neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1
as solvent, and a chain process was disregarded.
To further explore the possibility of dithiane anions as electron donors in a radical
nucleophilic substitution (SRN1),4 we have studied the reactions of 2-aryl-1,3-dithiane anions (1) with
neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1
neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1
neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1
as solvent, and a chain process was disregarded.
To further explore the possibility of dithiane anions as electron donors in a radical
nucleophilic substitution (SRN1),4 we have studied the reactions of 2-aryl-1,3-dithiane anions (1) with
neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1
neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1
neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1
aldehydes, ketones and carboxylic acid derivatives by polar mechanisms. Furthermore, the
participation of 2-lithio-1,3-dithiane as electron donor was suggested in the reaction with a
neopentyl-type radical probe 5,5-dimethyl-6-iodo-1-hexene, with formation of 6-11% of cyclized
alkylated product.3 These reactions were performed at very low temperature (-20°C) in THF or THFTMDA
as solvent, and a chain process was disregarded.
To further explore the possibility of dithiane anions as electron donors in a radical
nucleophilic substitution (SRN1),4 we have studied the reactions of 2-aryl-1,3-dithiane anions (1) with
neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1
neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1
neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1
as solvent, and a chain process was disregarded.
To further explore the possibility of dithiane anions as electron donors in a radical
nucleophilic substitution (SRN1),4 we have studied the reactions of 2-aryl-1,3-dithiane anions (1) with
neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1
neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1
neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1
as solvent, and a chain process was disregarded.
To further explore the possibility of dithiane anions as electron donors in a radical
nucleophilic substitution (SRN1),4 we have studied the reactions of 2-aryl-1,3-dithiane anions (1) with
neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1
neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1
neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1
products.2 These anions react with common electrophiles such as alkyl, allyl and benzyl halides,
aldehydes, ketones and carboxylic acid derivatives by polar mechanisms. Furthermore, the
participation of 2-lithio-1,3-dithiane as electron donor was suggested in the reaction with a
neopentyl-type radical probe 5,5-dimethyl-6-iodo-1-hexene, with formation of 6-11% of cyclized
alkylated product.3 These reactions were performed at very low temperature (-20°C) in THF or THFTMDA
as solvent, and a chain process was disregarded.
To further explore the possibility of dithiane anions as electron donors in a radical
nucleophilic substitution (SRN1),4 we have studied the reactions of 2-aryl-1,3-dithiane anions (1) with
neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1
neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1
neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1
as solvent, and a chain process was disregarded.
To further explore the possibility of dithiane anions as electron donors in a radical
nucleophilic substitution (SRN1),4 we have studied the reactions of 2-aryl-1,3-dithiane anions (1) with
neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1
neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1
neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1
as solvent, and a chain process was disregarded.
To further explore the possibility of dithiane anions as electron donors in a radical
nucleophilic substitution (SRN1),4 we have studied the reactions of 2-aryl-1,3-dithiane anions (1) with
neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1
neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1
neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1
aldehydes, ketones and carboxylic acid derivatives by polar mechanisms. Furthermore, the
participation of 2-lithio-1,3-dithiane as electron donor was suggested in the reaction with a
neopentyl-type radical probe 5,5-dimethyl-6-iodo-1-hexene, with formation of 6-11% of cyclized
alkylated product.3 These reactions were performed at very low temperature (-20°C) in THF or THFTMDA
as solvent, and a chain process was disregarded.
To further explore the possibility of dithiane anions as electron donors in a radical
nucleophilic substitution (SRN1),4 we have studied the reactions of 2-aryl-1,3-dithiane anions (1) with
neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1
neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1
neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1
as solvent, and a chain process was disregarded.
To further explore the possibility of dithiane anions as electron donors in a radical
nucleophilic substitution (SRN1),4 we have studied the r